IL34830A - N-formyl-alpha-nitro-alkane carboxylic acid amides and their production - Google Patents
N-formyl-alpha-nitro-alkane carboxylic acid amides and their productionInfo
- Publication number
- IL34830A IL34830A IL34830A IL3483070A IL34830A IL 34830 A IL34830 A IL 34830A IL 34830 A IL34830 A IL 34830A IL 3483070 A IL3483070 A IL 3483070A IL 34830 A IL34830 A IL 34830A
- Authority
- IL
- Israel
- Prior art keywords
- carboxylic acid
- process according
- nitro
- formula
- acid
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims description 16
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 12
- -1 alkane carboxylic acid Chemical class 0.000 claims description 10
- 239000003795 chemical substances by application Substances 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 10
- 230000000802 nitrating effect Effects 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 230000002140 halogenating effect Effects 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 9
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
- 239000000010 aprotic solvent Substances 0.000 claims description 6
- 239000003085 diluting agent Substances 0.000 claims description 5
- 229910017604 nitric acid Inorganic materials 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 238000006396 nitration reaction Methods 0.000 claims description 4
- 150000003335 secondary amines Chemical class 0.000 claims description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 4
- 239000013067 intermediate product Substances 0.000 claims description 3
- PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 claims description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- 230000003301 hydrolyzing effect Effects 0.000 claims description 2
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 claims description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- 229910052698 phosphorus Inorganic materials 0.000 claims 1
- 239000011574 phosphorus Substances 0.000 claims 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 claims 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- MNWFXJYAOYHMED-UHFFFAOYSA-N hexane carboxylic acid Natural products CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical class CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical class CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 3
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical class CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 3
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical class CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 3
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical class CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 description 3
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical class CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 3
- 238000004821 distillation Methods 0.000 description 2
- 150000003948 formamides Chemical class 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 2
- FGKJLKRYENPLQH-UHFFFAOYSA-N isocaproic acid Chemical compound CC(C)CCC(O)=O FGKJLKRYENPLQH-UHFFFAOYSA-N 0.000 description 2
- LCEDQNDDFOCWGG-UHFFFAOYSA-N morpholine-4-carbaldehyde Chemical compound O=CN1CCOCC1 LCEDQNDDFOCWGG-UHFFFAOYSA-N 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 2
- TUNFSRHWOTWDNC-UHFFFAOYSA-N tetradecanoic acid Chemical class CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 description 2
- XYHKNCXZYYTLRG-UHFFFAOYSA-N 1h-imidazole-2-carbaldehyde Chemical compound O=CC1=NC=CN1 XYHKNCXZYYTLRG-UHFFFAOYSA-N 0.000 description 1
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
- TWJNQYPJQDRXPH-UHFFFAOYSA-N 2-cyanobenzohydrazide Chemical compound NNC(=O)C1=CC=CC=C1C#N TWJNQYPJQDRXPH-UHFFFAOYSA-N 0.000 description 1
- WLAMNBDJUVNPJU-UHFFFAOYSA-N 2-methylbutyric acid Chemical compound CCC(C)C(O)=O WLAMNBDJUVNPJU-UHFFFAOYSA-N 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-M 3-Methylbutanoic acid Natural products CC(C)CC([O-])=O GWYFCOCPABKNJV-UHFFFAOYSA-M 0.000 description 1
- 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 description 1
- 239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical class CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- 239000005639 Lauric acid Substances 0.000 description 1
- 235000021360 Myristic acid Nutrition 0.000 description 1
- 239000005643 Pelargonic acid Substances 0.000 description 1
- LJTZDGRRKZDLHP-UHFFFAOYSA-N [P].[Cl].[Cl].[Cl].[Cl].[Cl] Chemical compound [P].[Cl].[Cl].[Cl].[Cl].[Cl] LJTZDGRRKZDLHP-UHFFFAOYSA-N 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- AQIHMSVIAGNIDM-UHFFFAOYSA-N benzoyl bromide Chemical compound BrC(=O)C1=CC=CC=C1 AQIHMSVIAGNIDM-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N beta-methyl-butyric acid Natural products CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- RGXCTRIQQODGIZ-UHFFFAOYSA-O isodesmosine Chemical compound OC(=O)C(N)CCCC[N+]1=CC(CCC(N)C(O)=O)=CC(CCC(N)C(O)=O)=C1CCCC(N)C(O)=O RGXCTRIQQODGIZ-UHFFFAOYSA-O 0.000 description 1
- MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical compound [NH-]C MGJXBDMLVWIYOQ-UHFFFAOYSA-N 0.000 description 1
- IXHFNEAFAWRVCF-UHFFFAOYSA-N n,2-dimethylpropanamide Chemical compound CNC(=O)C(C)C IXHFNEAFAWRVCF-UHFFFAOYSA-N 0.000 description 1
- GFWZPTGIVKRQNM-UHFFFAOYSA-N n,3-dimethylbutanamide Chemical compound CNC(=O)CC(C)C GFWZPTGIVKRQNM-UHFFFAOYSA-N 0.000 description 1
- JIKUXBYRTXDNIY-UHFFFAOYSA-N n-methyl-n-phenylformamide Chemical compound O=CN(C)C1=CC=CC=C1 JIKUXBYRTXDNIY-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 229960002446 octanoic acid Drugs 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- UXCDUFKZSUBXGM-UHFFFAOYSA-N phosphoric tribromide Chemical compound BrP(Br)(Br)=O UXCDUFKZSUBXGM-UHFFFAOYSA-N 0.000 description 1
- SXBRULKJHUOQCD-UHFFFAOYSA-N propanoic acid Chemical compound CCC(O)=O.CCC(O)=O SXBRULKJHUOQCD-UHFFFAOYSA-N 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- SZHOJFHSIKHZHA-UHFFFAOYSA-N tridecanoic acid Chemical class CCCCCCCCCCCCC(O)=O SZHOJFHSIKHZHA-UHFFFAOYSA-N 0.000 description 1
- ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
The invention concerns new N-formyl-a-nitro-alkane carbox- ylic acid amides and a process for the production thereof.
From the literature it is known to react activated aromatic compounds with a formylating agent based on an N-disubstituted formamide and a halogenating agent for the production of aldehydes (Vilsmeier-Haak reaction) .
According to the present invention, N-formyl-a-nitro-alkane carboxylic acid amides of the Formula I ° wherein R^ represents an alkyl radical having 2 to 12 carbon atoms , and R2 and R^ independently of each other each represent a lower alkyl radical, are produced by reacting an alkane carboxylic acid amide of the 5 Formula II wherein R^, and have the meaning given for Formula I, with the formamide of a secondary amine and a halogenating agent, nitrating the complex intermediate thus obtained at a temperature between -10 and +30°C, and then hydrolyzing it at a temperature below +30°C.
For the process according to the invention, the starting materials N-alkyl-carboxylic acid amide, formamide and halogenating agent are preferably employed in a molar ratio of 1:1:2. The formamide can, however, also be employed in a multiple of the molar amount, the excess serving as solvent and/or diluent. In general, an aprotic solvent or diluent is necessary in the reaction forming the complex compound. Besides formamide, aliphatic halogenated hydrocarbons such as dichloromethane , chloroform, chlortanated ethanes, aromatic hydrocarbons and halcgenated hydrocarbons, as well as ether and ether-type compounds, etc. may be employed as aprotic solvents and diluents. Aprotic solvents are those which do not give off protons under the given reaction conditions.
Suitable as carboxylic acid amides of Formula II are the N-lower alkyl amides of the following alkane carboxylic acids: ethane carboxylic acid (propionic acid) , propane carboxylic acids (butyric acid, isobutyric acid), butane carboxylic acid (valeric acid, isovaleric acid, butane-2-carboxylic acid), pentane carboxylic acids (caproic acid, isocaproic acid, etc.), hexane carboxylic acid (enanthic acid, etc.), heptane carboxylic acids (caprylic acid, etc.), octane carboxylic acids (pelargonic acid, etc.), nonane carboxylic acids (capric acid, etc.), decane carboxylic a cids , undecane carboxylic acids (e.g. lauric acid), dodecane carboxylic acids, tridecane carboxylic acids (myristic acid) .
The formaraides of secondary amines employed correspond to the Formula III R' .
N - CHO (III) Ru In this formula: R' represents an alkyl radical having 1 to 5 carbon atoms R" represents an alkyl radical having 1 to 5 carbon atoms a phenyl, benzyl or cycloalkyl radical, or R' and RM together with the adjacent nitrogen atom represent a heterocyclic ring which can contain further hetero atoms.
Preferably the following formamides of Formula III are employed: N ,N-dimethylformamide , ,N-diethylformamide , N-methyl-formanilide, N- formylmorpholine , in particular, however, N,N-di-methyIformamide .
Suitable as halogenating agents are, in particular, the halides of the following inorganic oxyacids: phosphorus oxy-chloride, phosphorus trichloride, phosphorus pentachlor.ide , phosphorus tribromide, phosphorus oxybromide, thionyl chloride, sulfuryl chloride, phosgene, oxalyl chloride or benzoyl bromide.
For the nitration, preferably nitrating acid, i.e. a mixture of concentrated or fuming nitric acid and concentrated sulfuric acid, is used. In order to attain as quantitative a nitration as possible, it is advantageous to use the nitrating acid in excess; preferably the double to fivefold molar amount of HNO^ is used, calculated on the amount of alkane carboxylic acid amide used. When a nitrating acid consisting of concentrated nitric acid, concentrated sulfuric acid and sulfur trioxide is used, the molar ratio of nitric acid to alkane carboxylic acid amide can be 1:1.
When performing the process according to the invention, it has proved expedient to start with the formamide, adding the halogenating agent at temperatures between 0° and 40°C, preferably between 0° and 10°C, while stirring thoroughly. When the formamide is used in equimolar amounts, calculated on the carboxylic acid amide, it is necessary to perform the reaction in the presence of an organic aprotic solvent or diluent. Then the alkane carboxylic acid amide is added. Both of the last-mentioned reaction components , the halogenating agent and the alkane carboxylic acid amide, can be employed in the reaction dissolved in one of the aprotic solvents mentioned above such as benzene, chloroform, etc. To increase the velocity of the . reaction, which in itself proceeds smoothly at temperatures in the range of 0 to 40°C, the reaction mixture can be heated to temperatures of not more than 120°C, preferably to 60 to 85' C. After completion of the reaction, it is expedient to remove the solvent at 0 to 40°C in vacuum and to add the complex intermediate product obtained directly to the nitrating acid. Also for this step in the nitration, it is essential that the temperature be kept below 30CC, preferably at 10°C. The nitrating mixture is finally hydrolyzed with ice water, the temperature not being more than 30°C, preferably not more than 15°C.
The new N-formyl-a-nitro-alkane carboxylic acid amides are obtained according to the invention in very good yields.. They are important intermediates from which, by reduction of the nitro group and subsequent hydrolosis a-amino acids are produced.
The following examples illustrate the invention. ' The temperatures are given in degrees centigrade and the boiling points are uncorrected.
Exam le 1 11.9 ml of di eth lformamide in 250 ml of chloroform are treated dropwise at 0 to 5° with 26.3 ml of phosphorus oxychloride. The mixture' is then stirred, for one hour at 5° , then treated with a solution of 13.6 g of isobutyric acid-methyl amide : 1.4405, b.p. 56- 0° /0.005 Torr) in 120 ml of chloroform, stirred for one hour at room temperature and then refluxed for 10 hours. The reaction mixture is then cooled and concentrated in vacuum. A nitrating mixture obtained from 22 ml of concentrated nitric acid and 120 ml of concentrated sulfuric acid is then added dropwise to the residue at 0 to 10°with stirring. The mixture is then poured onto ice and extracted several times with chloroform. After drying and removal of the chloroform by distillation, the residue is fractionated in vacuum. The cc-nitro-isobutyric acid-N- formy1-N-methyl-amide has a boiling on point of 75-85°/0.001 Torr. Refraction index nD = 1.4780.
Example 2 12 ml of dimethylformamide and 100 ml of chloroform are treated dropwise at 20° with 26.3 ml of phosphorus oxychloride and stirred for 30 minutes at the same temperature. The mixture is then treated dropwise at 20° with a solution of 15.2 g of isovaleric acid-N-methylamide (b.p. 74-76V0.01 Torr, refraction index ηβ = 1.4444), stirred for one hour at 20° and subsequently refluxed for 10 hours.. The mixture is then concentrated in vacuum. The. residue is treated dropwise at 0 to 10a with a nitrating mixture obtained from 22 ml of concentrated nitric acid and 120 ml of concentrated sulfuric acid, then poured onto ice and extracted with chloroform. After cooling and removal of the solvent by distillation, the residue is fractionated in vacuum. The a-nitro-isovaleric acid-N-formyl-N-methylamide has a boiling point of 80-90°/0.001 Torr, refraction index r^20 = 1.4764.
In the manner described in the preceding examples , using the appropriate carboxylic acid amides of Formula II, dimethyl- formamide and phosphorus oxychloride, there are obtained the compounds listed in the following table: Compound physical data a-nitro-lauric acid-N-formyl- b.p. 145- 150° 10.05 Torr N-methylamide a-nitro-lauric acid-N-formyl- N-n-butylamide
Claims (8)
1. N-Formyl-a-nitro-alkane carboxylic acid amides of the Formula I R, 0 0 (I) I N - CHO - wherein represents an alkyl radical having 2 to 12 carbon atoms , and R and R¾ independently of each other each represent a lower alkyl radical.
2. Process for the production of N- formyl-a-nitro-alkane carboxylic acid amides of the Formula I R wherein , R2 and R^ have the meanings given for Formula I in Claim 1, characterized by reacting an alkane carboxylic acid of the Formula II (II) with the formamide of a secondary amine and a halogenating agent, nitrating the complex intermediate product obtained and subsequently hydrolyzing it.
3. Process according to Claim 2, characterized by employ ing dimethylformamide as formamide of a secondary amine, and halides of inorganic oxyacids as halogenating agent.
4. A. Process according to Claims 2 and 3, characterized by employing phosphorus trichloride, phosphorus tribromide, phosphorus oxyehloride, phosphorus pentachloride , phosgene or thionyl chloride as halogenating agent,
5. Process according to Claim 2, characterized by performing the nitration with a . mixture consisting of nitric acid and sulfuric acid.
6. Process according to Claims 2 and 5, characterized by nitrating the intermediate product at temperatures between -10 and +30° C.
7. Process according to Claims 2 and 5, characterized by performing the hydrolysis at temperatures below +30° C.
8. Process according to Claim 2, characterized by performing the reaction in the presence of organic aprotic solvents and/or diluents.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1011169A CH515891A (en) | 1969-07-02 | 1969-07-02 | Process for the preparation of N-formyl-a-nitro-alkanecarboxamides |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL34830A0 IL34830A0 (en) | 1971-02-25 |
| IL34830A true IL34830A (en) | 1973-05-31 |
Family
ID=4359466
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL34830A IL34830A (en) | 1969-07-02 | 1970-07-01 | N-formyl-alpha-nitro-alkane carboxylic acid amides and their production |
Country Status (7)
| Country | Link |
|---|---|
| BE (1) | BE752812A (en) |
| CH (1) | CH515891A (en) |
| DE (1) | DE2032628A1 (en) |
| FR (1) | FR2053970A5 (en) |
| GB (1) | GB1320408A (en) |
| IL (1) | IL34830A (en) |
| NL (1) | NL7009728A (en) |
-
1969
- 1969-07-02 CH CH1011169A patent/CH515891A/en not_active IP Right Cessation
-
1970
- 1970-07-01 GB GB3185370A patent/GB1320408A/en not_active Expired
- 1970-07-01 DE DE19702032628 patent/DE2032628A1/en active Granted
- 1970-07-01 IL IL34830A patent/IL34830A/en unknown
- 1970-07-01 FR FR7024372A patent/FR2053970A5/fr not_active Expired
- 1970-07-01 NL NL7009728A patent/NL7009728A/xx unknown
- 1970-07-01 BE BE752812D patent/BE752812A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FR2053970A5 (en) | 1971-04-16 |
| BE752812A (en) | 1971-01-04 |
| GB1320408A (en) | 1973-06-13 |
| IL34830A0 (en) | 1971-02-25 |
| CH515891A (en) | 1971-11-30 |
| NL7009728A (en) | 1971-01-05 |
| DE2032628A1 (en) | 1971-07-22 |
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