NO115568B - - Google Patents
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- NO115568B NO115568B NO159398A NO15939865A NO115568B NO 115568 B NO115568 B NO 115568B NO 159398 A NO159398 A NO 159398A NO 15939865 A NO15939865 A NO 15939865A NO 115568 B NO115568 B NO 115568B
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- Prior art keywords
- formula
- diol
- added
- phenyl
- nitrophenyl
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- 150000001923 cyclic compounds Chemical class 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 4
- 239000007858 starting material Substances 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 230000000802 nitrating effect Effects 0.000 claims description 2
- 125000006501 nitrophenyl group Chemical group 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 239000000047 product Substances 0.000 description 19
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 17
- 125000004122 cyclic group Chemical group 0.000 description 15
- 239000011541 reaction mixture Substances 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- 239000007787 solid Substances 0.000 description 14
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 12
- 238000003756 stirring Methods 0.000 description 11
- 150000005676 cyclic carbonates Chemical class 0.000 description 10
- 229910017604 nitric acid Inorganic materials 0.000 description 9
- 238000001953 recrystallisation Methods 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 239000000203 mixture Substances 0.000 description 4
- 230000004048 modification Effects 0.000 description 4
- 238000012986 modification Methods 0.000 description 4
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 230000003115 biocidal effect Effects 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000006396 nitration reaction Methods 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 239000012265 solid product Substances 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000000185 1,3-diols Chemical class 0.000 description 1
- YTBSYETUWUMLBZ-QWWZWVQMSA-N D-threose Chemical compound OC[C@@H](O)[C@H](O)C=O YTBSYETUWUMLBZ-QWWZWVQMSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- KWGRBVOPPLSCSI-UHFFFAOYSA-N d-ephedrine Natural products CNC(C)C(O)C1=CC=CC=C1 KWGRBVOPPLSCSI-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- KWGRBVOPPLSCSI-WCBMZHEXSA-N pseudoephedrine Chemical compound CN[C@@H](C)[C@@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WCBMZHEXSA-N 0.000 description 1
- 229960003908 pseudoephedrine Drugs 0.000 description 1
Classifications
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F42—AMMUNITION; BLASTING
- F42B—EXPLOSIVE CHARGES, e.g. FOR BLASTING, FIREWORKS, AMMUNITION
- F42B12/00—Projectiles, missiles or mines characterised by the warhead, the intended effect, or the material
- F42B12/02—Projectiles, missiles or mines characterised by the warhead, the intended effect, or the material characterised by the warhead or the intended effect
- F42B12/36—Projectiles, missiles or mines characterised by the warhead, the intended effect, or the material characterised by the warhead or the intended effect for dispensing materials; for producing chemical or physical reaction; for signalling ; for transmitting information
- F42B12/46—Projectiles, missiles or mines characterised by the warhead, the intended effect, or the material characterised by the warhead or the intended effect for dispensing materials; for producing chemical or physical reaction; for signalling ; for transmitting information for dispensing gases, vapours, powders or chemically-reactive substances
- F42B12/48—Projectiles, missiles or mines characterised by the warhead, the intended effect, or the material characterised by the warhead or the intended effect for dispensing materials; for producing chemical or physical reaction; for signalling ; for transmitting information for dispensing gases, vapours, powders or chemically-reactive substances smoke-producing, e.g. infrared clouds
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F42—AMMUNITION; BLASTING
- F42B—EXPLOSIVE CHARGES, e.g. FOR BLASTING, FIREWORKS, AMMUNITION
- F42B12/00—Projectiles, missiles or mines characterised by the warhead, the intended effect, or the material
- F42B12/02—Projectiles, missiles or mines characterised by the warhead, the intended effect, or the material characterised by the warhead or the intended effect
- F42B12/36—Projectiles, missiles or mines characterised by the warhead, the intended effect, or the material characterised by the warhead or the intended effect for dispensing materials; for producing chemical or physical reaction; for signalling ; for transmitting information
- F42B12/38—Projectiles, missiles or mines characterised by the warhead, the intended effect, or the material characterised by the warhead or the intended effect for dispensing materials; for producing chemical or physical reaction; for signalling ; for transmitting information of tracer type
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F42—AMMUNITION; BLASTING
- F42B—EXPLOSIVE CHARGES, e.g. FOR BLASTING, FIREWORKS, AMMUNITION
- F42B12/00—Projectiles, missiles or mines characterised by the warhead, the intended effect, or the material
- F42B12/02—Projectiles, missiles or mines characterised by the warhead, the intended effect, or the material characterised by the warhead or the intended effect
- F42B12/36—Projectiles, missiles or mines characterised by the warhead, the intended effect, or the material characterised by the warhead or the intended effect for dispensing materials; for producing chemical or physical reaction; for signalling ; for transmitting information
- F42B12/42—Projectiles, missiles or mines characterised by the warhead, the intended effect, or the material characterised by the warhead or the intended effect for dispensing materials; for producing chemical or physical reaction; for signalling ; for transmitting information of illuminating type, e.g. carrying flares
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F42—AMMUNITION; BLASTING
- F42B—EXPLOSIVE CHARGES, e.g. FOR BLASTING, FIREWORKS, AMMUNITION
- F42B8/00—Practice or training ammunition
- F42B8/02—Cartridges
Landscapes
- Engineering & Computer Science (AREA)
- General Engineering & Computer Science (AREA)
- Chemical & Material Sciences (AREA)
- Combustion & Propulsion (AREA)
- Aiming, Guidance, Guns With A Light Source, Armor, Camouflage, And Targets (AREA)
- Catching Or Destruction (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Portable Nailing Machines And Staplers (AREA)
Description
Fremgangsmåte til fremstilling av nitrofenylsubstituerte cykliske forbindelser. Process for the preparation of nitrophenyl substituted cyclic compounds.
Foreliggende oppfinnelse angår en The present invention relates to a
fremgangsmåte til fremstilling av med ni-trofenyl substituerte cykliske forbindelser process for the preparation of nitrophenyl-substituted cyclic compounds
med den generelle formel with the general formula
i hvilken Ri betyr vannstoff, halogen, et in which Ri means hydrogen, halogen, et
loucro ol Inrlra Hi Va 1 ollor ot- a lVnVc-wra rii Ira 1 loucro ol Inrlra Hi Va 1 ollor ot- a lVnVc-wra rii Ira 1
og betegner en - SO - eller - CO - gruppe. and denotes a - SO - or - CO - group.
Med uttrykket «acyl» som det brukes her With the term "acyl" as used herein
menes karbonsyre-acylradikaler som lavere carboxylic acid acyl radicals are meant as lower
alifatiske acyl-, halogenerte lavere alifatiske acyl-, umettede lavere alifatiske acyl-, aliphatic acyl-, halogenated lower aliphatic acyl-, unsaturated lower aliphatic acyl-,
etersubstituerte lavere alifatiske acyl-, ether-substituted lower aliphatic acyl-,
benzoyl-, nitrerte benzoyl-, alkylerte benzoyl-, aralifatiske acylradikaler og lignende radikaler. benzoyl, nitrated benzoyl, alkylated benzoyl, araliphatic acyl radicals and similar radicals.
Av den følgende beskrivelse vil det være Of the following description it will be
klart for fagmannen at både utgangsmate-rialene og produktene i fremgangsmåten clear to the person skilled in the art that both the starting materials and the products in the method
ifølge oppfinnelsen eksisterer i strukturelle according to the invention exist in structural
eller diastereoisomere modifikasjoner såvel or diastereoisomeric modifications as well
som i optisk isomere modifikasjoner. Foreliggende oppfinnelse angår forbindelser i as in optically isomeric modifications. The present invention relates to compounds i
den «pseudo»-diastereoisomere modifikasjon til forskjell fra den «regulære» diastereoisomere modifikasjon. Gruppene på de the "pseudo" diastereoisomeric modification as distinct from the "regular" diastereoisomeric modification. The groups on them
to asymmetriske kullstoffatomer i slike two asymmetric carbon atoms in such
pseudo-diastereoisomere har samme rom-lige konfigurasjon som gruppene på de to pseudo-diastereoisomers have the same spatial configuration as the groups on the two
asymmetriske kullstoffatomer i pseudoefe-drin og treose. asymmetric carbon atoms in pseudoephedrine and threose.
På grunn av vanskelighetene ved å vise disse strukturelle forskjelligheter i grafiske formler vil de vanlige strukturformler bli brukt i denne beskrivelse og patentpåstan-dene og der vil bli anbragt en betegnelse under eller til siden for formlen for å vise forbindelsens særlige strukturelle og op-tiske konfigurasjon. Når betegnelsen «ip-form» brukes skal formlen tolkes generelt, dvs. den betyr både den hpisomere og den d-i|) isomere adskilt, såvel som den rasemiske blanding. En slik formel betyr altså ikke bare den optisk rasemiske blanding. Due to the difficulties in showing these structural differences in graphical formulas, the usual structural formulas will be used in this description and the patent claims and a designation will be placed below or to the side of the formula to show the particular structural and optical configuration of the compound . When the term "ip-form" is used, the formula is to be interpreted generally, i.e. it means both the hpisomer and the d-i|) isomer separately, as well as the racemic mixture. Such a formula does not mean only the optical racemic mixture.
Ifølge oppfinnelsen underkastes fenylsubstituerte cykliske forbindelser med den generelle formel According to the invention, phenyl-substituted cyclic compounds of the general formula are submitted
nitrering så at man får fenylsubstituerte cykliske forbindelser med den generelle formel: nitration so that one obtains phenyl-substituted cyclic compounds with the general formula:
I disse formler har Ri og Y den foran angitte betydning. In these formulas, Ri and Y have the meaning indicated above.
Nitreringen av den fenylsubstituerte cykliske forbindelses fenylring utføres ved hjelp av rykende salpetersyre, 100 pst.s salpetersyre eller en blanding av konsentrert salpetersyre og konsentrert svovelsyre som nitreringsmiddel. Temperaturen under denne reaksjon bør holdes under ca. 10° C og fortrinsvis under —10° C. The nitration of the phenyl-substituted cyclic compound's phenyl ring is carried out using fuming nitric acid, 100% nitric acid or a mixture of concentrated nitric acid and concentrated sulfuric acid as nitrating agent. The temperature during this reaction should be kept below approx. 10° C and preferably below -10° C.
De produketr man får ved fremgangsmåten ifølge foreliggende oppfinnelse har antibiotisk virkning og er nyttige som mel-lomprodukter ved fremstilling av organiske forbindelser med antibiotisk virkning og særlig av dl- og l-pseudo^l-p-nitrofenyl-2-dikloracetamido-propan-l-,3-dioler. The products obtained by the method according to the present invention have antibiotic action and are useful as intermediates in the production of organic compounds with antibiotic action and in particular of dl- and l-pseudo^l-p-nitrophenyl-2-dichloroacetamido-propane-l-, 3-diols.
De fenylsubstituerte cykliske forbindelser som brukes som utgangsmaterialer i fremgangsmåten ifølge foreliggende oppfinnelse kan fremstilles ved hjelp av den metode som er beskrevet i patent nr. 86448. The phenyl-substituted cyclic compounds which are used as starting materials in the method according to the present invention can be prepared using the method described in patent no. 86448.
I det følgende beskrives som eksempler noen utførelsesformer for oppfinnelsen. In the following, some embodiments of the invention are described as examples.
Eksempel 1: Example 1:
10 g av det cykliske sulfit av dl-ip-l-fenyl-2-dikloracetamidopropan-l,3-diol med formlen tilsettes i små porsjoner og under omrø-ring til 50 cc. 100 pst.s salpetersyre som er avkjølt til ca. —30° C ved tilsetning av fast kullsyre. Etter at reaksjonen er full-stendig helles reaksjonsblandingen på knust is og det hvite faste stoff som skiller seg ut oppsamles. Dette produkt som er det cykliske sulfit av dl-ap-l-p-nitrofenyl-2-dikloracetamidopropan-l,3-diol kan om øn-skes renses ved omkrystallisasjon fra etanol. Produktets sm.p. er 175—176° C og det har formlen 10 g of the cyclic sulfite of dl-ip-l-phenyl-2-dichloroacetamidopropane-l,3-diol of the formula is added in small portions and while stirring to 50 cc. 100 percent nitric acid that has been cooled to approx. -30° C when solid carbon dioxide is added. After the reaction is complete, the reaction mixture is poured onto crushed ice and the white solid that separates is collected. This product, which is the cyclic sulfite of dl-ap-1-p-nitrophenyl-2-dichloroacetamidopropane-1,3-diol, can, if desired, be purified by recrystallization from ethanol. The product's m.p. is 175-176° C and it has the formula
Man får lignende resultater hvis man i stedet for 100 pst.s salpetersyre som angitt ovenfor bruker rykende salpetersyre eller en blanding av konsentrert salpetersyre og konsentrert svovelsyre. Similar results are obtained if, instead of 100% nitric acid as stated above, fuming nitric acid or a mixture of concentrated nitric acid and concentrated sulfuric acid is used.
Eksempel 2: Example 2:
9 g av det cykliske karbonat av dl-i|j-l-f enyl-2-dikloracetamidopropan-l,3-diol med formelen tilsettes i små porsjoner og under omrøring til 30 cm'<1> rykende salpetersyre som holdes på 20° C ved tilsetning av små porsjoner av fast kullsyre. Etter at alt er tilsatt helles reaksjonsblandingen på is og det hvite produkt oppsamles. Dette faste produkt omkrystalliseres først fra eter og derpå fra metanol, hvorved man får det rene cykliske karbonat av dl-ip-l-p-nitrofenyl-2-dikloracetamidopropan-l,3-diol. Dette produkt smelter ved 180—185° C. Dets formel er 9 g of the cyclic carbonate of dl-i|j-l-phenyl-2-dichloroacetamidopropane-1,3-diol with the formula is added in small portions and with stirring to 30 cm'<1> of fuming nitric acid which is kept at 20° C by the addition of small portions of solid carbonic acid. After everything has been added, the reaction mixture is poured onto ice and the white product is collected. This solid product is first recrystallized from ether and then from methanol, whereby the pure cyclic carbonate of dl-ip-1-p-nitrophenyl-2-dichloroacetamidopropane-1,3-diol is obtained. This product melts at 180-185° C. Its formula is
Eksempel 3: Example 3:
9,5 g av det cykliske sulfit av l-i|)-l-fenyl-2-dikloracetamidopropan-l,3-diol med formlen tilsettes i små porsjoner og under omrøring til 50 cm* rykende salpetersyre ved —30° C. Under tilsetningen holdes temperaturen på omkring —20° C ved tilsetning av fast kullsyre. Etter at alt er tilsatt blir reaksjonsblandingen helt på knust is og det hvite faste cykliske sulfit av l-a|j-l-p-nitro-fenyl-2-dikloracetamidopropan-l,3-diol oppsamles. Etter omkrystallisasjon fraeta-nol smelter det rene produkt ved 171— 172° C. Dette produkts formel er 9.5 g of the cyclic sulphite of 1-(1)-1-phenyl-2-dichloroacetamidopropane-1,3-diol of the formula is added in small portions and with stirring to 50 cm* of fuming nitric acid at -30° C. During the addition, the temperature is kept at around -20° C by adding solid carbonic acid. After everything is added, the reaction mixture is poured onto crushed ice and the white solid cyclic sulfite of 1-a|j-1-p-nitro-phenyl-2-dichloroacetamidopropane-1,3-diol is collected. After recrystallization from ethanol, the pure product melts at 171-172° C. The formula of this product is
Eksempel 4: Example 4:
15 g av det cykliske karbonat av l-\\ >-l-fenyl-2-dikloracetamidopropan-l,3-diol med formlen tilsettes i små porsjoner og under omrø-ring til 45 cm<3> rykende salpetersyre ved —20° C. Under tilsetningen holdes temperaturen på —20° C ved tilsetning av små mengder fast kullsyre til reaksjonsblandingen. Etter at alt cyklisk karbonat er tilsatt helles reaksjonsblandingen på et stort volum is. Det uoppløselige hvite cykliske karbonat av l-i|)-l-p-nitrofenyl-2-dikloracetamidopropan-l,3-diol oppsamles, vaskes med vann og omkrystalliseres fra metanol. Dette produkts smeltepunkt er 157° C og det har formlen 15 g of the cyclic carbonate of l-\\>-l-phenyl-2-dichloroacetamidopropane-l,3-diol with the formula is added in small portions and with stirring to 45 cm<3> of fuming nitric acid at -20° C. During the addition, the temperature is kept at -20° C by adding small amounts of solid carbonic acid to the reaction mixture. After all the cyclic carbonate has been added, the reaction mixture is poured onto a large volume of ice. The insoluble white cyclic carbonate of 1-(1)-1-p-nitrophenyl-2-dichloroacetamidopropane-1,3-diol is collected, washed with water and recrystallized from methanol. This product's melting point is 157°C and it has the formula
Eksempel 5: Example 5:
12 g av det cykliske sulfit av dl-\|)-l-fenyl-2-benzamidopropan-l,3-diol med formlen tilsettes i små porsjoner og under omrø-ring til 75 cm'<1> rykende salpetersyre ved —20° C. Under tilsetningen holdes temperaturen i nærheten av —20° C ved tilsetning av fast kullsyre. Etter at alt er tilsatt blir reaksjonsblandingen helt på et stort volum knust is og det hvite uoppløse-lige cykliske sulfit av dl-ip-l-p-nitrofenyl-2'-m-nitrobenzamidopropan-l,3-diol oppsamles. Produktet vaskes med vann og renses ved omkrystallisasjon fra etanol. Dets formel er 12 g of the cyclic sulphite of dl-\|)-l-phenyl-2-benzamidopropane-1,3-diol of the formula is added in small portions and with stirring to 75 cm'<1> of fuming nitric acid at -20° C. During the addition, the temperature is kept close to -20° C by adding solid carbonic acid. After everything has been added, the reaction mixture is poured onto a large volume of crushed ice and the white insoluble cyclic sulfite of dl-ip-1-p-nitrophenyl-2'-m-nitrobenzamidopropane-1,3-diol is collected. The product is washed with water and purified by recrystallization from ethanol. Its formula is
Eksempel 6: Example 6:
10 g av det cykliske karbonat av dl-oj^-l-fenyl-2-acetamidopropan-l,3-diol med formlen tilsettes i små porsjoner og under om-røring til 30 cm<3> rykende salpetersyre. Under tilsetningen holdes temperaturen på —15 til —20° C ved tilsetning av små porsjoner av fast kullsyre. Etter at alt er tilsatt helles reaksjonsblandingen på is og det hvite faste produkt oppsamles. Produktet omkrystalliseres fra metanol, hvorved man får det rene cykliske karbonat av di-i|>-l-p-nitrofenyl-2-acetamidopropan~ 1,3-diol. Dette produkts formel er: 10 g of the cyclic carbonate of dl-oj^-1-phenyl-2-acetamidopropane-1,3-diol with the formula is added in small portions and while stirring to 30 cm<3> fuming nitric acid. During the addition, the temperature is kept at -15 to -20° C by adding small portions of solid carbonic acid. After everything has been added, the reaction mixture is poured onto ice and the white solid product is collected. The product is recrystallized from methanol, whereby the pure cyclic carbonate of di-i>-1-p-nitrophenyl-2-acetamidopropane~ 1,3-diol is obtained. This product's formula is:
Eksempel 7: Example 7:
14,5 g av det cykliske sulfit av dl-ap-1-fenyl-2-acetamidopropan-1,3-diol med formlen tilsettes i små porsjoner og under omrøring ti) 65 cm<3> 100 pst.'s salpetersyre ved —25° C. Temperaturen under tilsetningen holdes på ca. —20° C ved tilsetning av fast kull syre. Etter at alt er tilsatt helles reaksjonsblandingen på knust is og det hvite uoppløselige cykliske sulfit av dl-\|>-l-p-nitrofenyl-2-acetamidopropan-l,3-diol oppsamles og renses ved omkrystallisasjon fra etanol. Produktet smelter ved 165—167° C under spaltning. Dette produkts formel er Eksempel 8: I 9,5 g av det cykliske sulfit av dl-ijj-l-(3'-metoksyf enyl) -2-f enylacetamidopropan-1,3-diol med formlen: tilsettes i små porsjoner og under omrø-ring til 50 cm<3> 100 pst.'s salpetersyre ved —20° C. Temperaturen holdes under tilsetningen på —20° C ved tilsetning av fast kullsyre til reaksjonsblandingen. Etter at alt er tilsatt helles reaksjonsblandingen på knust is og det hvite faste cykliske sulfit av dl-cp-l-(3'-metoksy-4'-nitrofenyl-2-p-nitrofenylacetamidopropan-l,3-diol oppsamles og renses ved omkrystallisasjon fra etanol. Dette produkts formel er: 14.5 g of the cyclic sulfite of dl-ap-1-phenyl-2-acetamidopropane-1,3-diol of the formula is added in small portions and while stirring ten) 65 cm<3> 100 per cent nitric acid at -25° C. The temperature during the addition is kept at approx. -20° C when solid coal is added acid. After everything has been added, the reaction mixture is poured onto crushed ice and the white insoluble cyclic sulphite of dl-\|>-l-p-nitrophenyl-2-acetamidopropane-1,3-diol is collected and purified by recrystallization from ethanol. The product melts at 165-167° C during decomposition. The formula of this product is Example 8: I 9.5 g of the cyclic sulfite of dl-ijj-1-(3'-methoxyphenyl)-2-phenylacetamidopropane-1,3-diol of the formula: is added in small portions and with stirring to 50 cm<3> 100% nitric acid at -20° C. The temperature is kept during the addition at -20° C by adding solid carbonic acid to the reaction mixture. After everything has been added, the reaction mixture is poured onto crushed ice and the white solid cyclic sulfite of dl-cp-1-(3'-methoxy-4'-nitrophenyl-2-p-nitrophenylacetamidopropane-1,3-diol is collected and purified by recrystallization from ethanol This product's formula is:
Eksempel 9: Example 9:
14 g av det cykliske sulfit av dl-i|>-1- (2'-metylf enyl) -2-metoksyacetamido-propan-l,3-diol med formlen tilsettes i små porsjoner og under omrø-ring til 75 cm<3> 100 pst.'s salpetersyre ved —30° C. Under tilsetningen holdes temperaturen på —30° C ved tilsetning av små porsjoner fast kullsyre til reaksjonsblandingen. Etter at alt er tilsatt helles reaksjonsblandingen på knust is og det hvite uoppløselige cykliske sulfit av dl-i|j-l-(2'-metyl-4'-nitrof enyl) -2-metoksyacetamido-propan-l,3-diol oppsamles, vaskes med vann og renses ved omkrystallisasjon fra etanol. Dette produkts formel er: 14 g of the cyclic sulfite of dl-1>-1-(2'-methylphenyl)-2-methoxyacetamido-propane-1,3-diol of the formula is added in small portions and with stirring to 75 cm<3> 100% nitric acid at -30° C. During the addition, the temperature is kept at -30° C by adding small portions of solid carbonic acid to the reaction mixture. After everything has been added, the reaction mixture is poured onto crushed ice and the white insoluble cyclic sulfite of dl-i|j-l-(2'-methyl-4'-nitrophenyl)-2-methoxyacetamido-propane-l,3-diol is collected, washed with water and purified by recrystallization from ethanol. This product's formula is:
Eksempel 10: Example 10:
15 g av det cykliske karbonat av l-ip-l-fenyl-2-benzamidopropan-l,3-diol med formlen tilsettes i små porsjoner og under omrø-ring til 60 cm<3> rykende salpetersyre ved —20° C. Reaksjonsblandingens tempera-tur holdes på ca. —20° C under tilsetningen ved å tilføre små mengder fast kullsyre. Etter at alt cyklisk karbonat er tilsatt helles reaksjonsblandingen på is og det uoppløselige cykliske karbonat av 1-ip-l-p-nitrofenyl-2-m-nitrobenzamidopropan-1,3-diol oppsamles. Produktet vaskes med vann og renses ved omkrystallisasjon fra metanol. Denne forbindelses formel er: 15 g of the cyclic carbonate of 1-ip-1-phenyl-2-benzamidopropane-1,3-diol with the formula is added in small portions and with stirring to 60 cm<3> of fuming nitric acid at -20° C. The temperature of the reaction mixture is kept at approx. -20° C during the addition by adding small amounts of solid carbon dioxide. After all the cyclic carbonate has been added, the reaction mixture is poured onto ice and the insoluble cyclic carbonate of 1-ip-1-p-nitrophenyl-2-m-nitrobenzamidopropane-1,3-diol is collected. The product is washed with water and purified by recrystallization from methanol. The formula of this compound is:
Eksempel 11: Example 11:
8,5 g av det cykliske sulfit av dl-vp-1-(2'-klorf enyl) -2- (a-brompropionamido) - propan-l,3-diol med formlen tilsettes i små porsjoner og under omrø-ring til 50 cm<3> 100 pst.'s salpetersyre ved —25° C. Under tilsetningen holdes temperaturen på ca. —25° C ved tilsetning av små mengder fast kullsyre. Etter at alt cyklisk sulfit er tilsatt helles reaksjonsblandingen på knust is og det uoppløselige hvite cykliske sulfit av dl-i|j-l-(2'-klor-5'-nitrof enyl) -2- (a-brompropionamido)pro-pan-l,3-diol oppsamles. Produktet vaskes med vann og renses ved omkrystallisasjon fra etanol. Dette produkts formel er: 8.5 g of the cyclic sulfite of dl-vp-1-(2'-chlorophenyl)-2-(α-bromopropionamido)-propane-1,3-diol of the formula is added in small portions and with stirring to 50 cm<3> 100 per cent nitric acid at -25° C. During the addition, the temperature is kept at approx. -25° C by adding small amounts of solid carbonic acid. After all the cyclic sulfite has been added, the reaction mixture is poured onto crushed ice and the insoluble white cyclic sulfite of dl-i|j-l-(2'-chloro-5'-nitrophenyl)-2-(a-bromopropionamido)prop-pan-l ,3-diol is collected. The product is washed with water and purified by recrystallization from ethanol. This product's formula is:
Claims (3)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DED0046147 | 1964-12-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO115568B true NO115568B (en) | 1968-10-21 |
Family
ID=7049527
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO159398A NO115568B (en) | 1964-12-24 | 1965-08-19 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US3361066A (en) |
| AT (1) | AT255938B (en) |
| BE (1) | BE674106A (en) |
| DE (1) | DE1428678C3 (en) |
| FR (1) | FR1461180A (en) |
| NL (1) | NL150906B (en) |
| NO (1) | NO115568B (en) |
| SE (1) | SE320300B (en) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4007690A (en) * | 1975-11-21 | 1977-02-15 | The United States Of America As Represented By The Secretary Of The Navy | Practice bomb signal for day or night operation |
| DE3146645A1 (en) * | 1981-11-25 | 1983-06-01 | Rheinmetall GmbH, 4000 Düsseldorf | DEVICE FOR THE CONTROLLED LIMITATION OF THE LETAL RANGE OF A TARGET MISSING A TARGET WITH A STABILIZING ELEMENT AND A LUMINAIRE TRACK |
| NO307154B1 (en) * | 1998-08-17 | 2000-02-14 | Raufoss Tech As | Creation rocket for smoke development |
| GB0306886D0 (en) * | 2003-03-26 | 2003-04-30 | Williams Janet E | Personal attack alarm |
| KR20130041309A (en) * | 2004-04-02 | 2013-04-24 | 테크벤쳐 인베스트먼트스 피티와이 엘티디 | Projectile |
| AU2013101363B4 (en) | 2013-07-31 | 2014-03-13 | Techventure Investments Pty Ltd | A projectile body and corresponding ammunition round for small arms or a light firearm |
| US9052175B1 (en) * | 2014-10-14 | 2015-06-09 | SCTA Associates, Trustee for Sabotage Cartridge with Toxic Agent CRT Trust | Sabotage cartridge with toxic agent |
| DE102017106333A1 (en) * | 2017-03-23 | 2018-09-27 | Rheinmetall Waffe Munition Gmbh | Adaptive projectile |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2900914A (en) * | 1958-03-11 | 1959-08-25 | Thomas Q Ciccone | Incendiary projectile |
| US3013495A (en) * | 1959-07-10 | 1961-12-19 | Stevenson Thomas | Spotter-tracer projectile |
| US3101054A (en) * | 1960-10-05 | 1963-08-20 | Stevenson Thomas | Electrically initiated spotter tracer bullet |
| NL300800A (en) * | 1962-11-21 |
-
1964
- 1964-12-24 DE DE1428678A patent/DE1428678C3/en not_active Expired
-
1965
- 1965-08-19 NO NO159398A patent/NO115568B/no unknown
- 1965-09-24 AT AT871265A patent/AT255938B/en active
- 1965-10-01 SE SE12751/65A patent/SE320300B/xx unknown
- 1965-11-03 NL NL656514249A patent/NL150906B/en unknown
- 1965-12-13 US US513430A patent/US3361066A/en not_active Expired - Lifetime
- 1965-12-21 BE BE674106D patent/BE674106A/xx unknown
- 1965-12-22 FR FR43379A patent/FR1461180A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| NL150906B (en) | 1976-09-15 |
| SE320300B (en) | 1970-02-02 |
| DE1428678C3 (en) | 1974-04-11 |
| US3361066A (en) | 1968-01-02 |
| NL6514249A (en) | 1966-06-27 |
| DE1428678B2 (en) | 1973-09-13 |
| FR1461180A (en) | 1966-12-02 |
| BE674106A (en) | 1966-04-15 |
| AT255938B (en) | 1967-07-25 |
| DE1428678A1 (en) | 1969-03-06 |
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