NO116185B - - Google Patents
Info
- Publication number
- NO116185B NO116185B NO159992A NO15999265A NO116185B NO 116185 B NO116185 B NO 116185B NO 159992 A NO159992 A NO 159992A NO 15999265 A NO15999265 A NO 15999265A NO 116185 B NO116185 B NO 116185B
- Authority
- NO
- Norway
- Prior art keywords
- alkylation
- sodium
- ethoxypropionitrile
- formyl
- salts
- Prior art date
Links
- 150000003839 salts Chemical class 0.000 claims description 11
- 230000029936 alkylation Effects 0.000 claims description 9
- 238000005804 alkylation reaction Methods 0.000 claims description 9
- 230000010933 acylation Effects 0.000 claims description 7
- 238000005917 acylation reaction Methods 0.000 claims description 7
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- -1 formic acid ester Chemical class 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 235000019253 formic acid Nutrition 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 4
- 159000000000 sodium salts Chemical class 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- SNJNVEVAILOJBB-UHFFFAOYSA-N 2-ethoxypropanenitrile Chemical compound CCOC(C)C#N SNJNVEVAILOJBB-UHFFFAOYSA-N 0.000 description 2
- OQLZINXFSUDMHM-UHFFFAOYSA-N Acetamidine Chemical compound CC(N)=N OQLZINXFSUDMHM-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 229930003270 Vitamin B Natural products 0.000 description 2
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 2
- 239000012346 acetyl chloride Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 2
- DZXBHDRHRFLQCJ-UHFFFAOYSA-M sodium;methyl sulfate Chemical compound [Na+].COS([O-])(=O)=O DZXBHDRHRFLQCJ-UHFFFAOYSA-M 0.000 description 2
- 235000019156 vitamin B Nutrition 0.000 description 2
- 239000011720 vitamin B Substances 0.000 description 2
- DNCYBUMDUBHIJZ-UHFFFAOYSA-N 1h-pyrimidin-6-one Chemical compound O=C1C=CN=CN1 DNCYBUMDUBHIJZ-UHFFFAOYSA-N 0.000 description 1
- TVXOUBKYDAZBIS-UHFFFAOYSA-N 2-(ethoxymethyl)-3-methoxyprop-2-enenitrile Chemical compound CCOCC(C#N)=COC TVXOUBKYDAZBIS-UHFFFAOYSA-N 0.000 description 1
- WSGYTJNNHPZFKR-UHFFFAOYSA-N 3-hydroxypropanenitrile Chemical compound OCCC#N WSGYTJNNHPZFKR-UHFFFAOYSA-N 0.000 description 1
- XTYHLMPMYGVQES-UHFFFAOYSA-N C(C)(=O)OC=C(C#N)COCC Chemical compound C(C)(=O)OC=C(C#N)COCC XTYHLMPMYGVQES-UHFFFAOYSA-N 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000005396 acrylic acid ester group Chemical group 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Classifications
-
- E—FIXED CONSTRUCTIONS
- E21—EARTH DRILLING; MINING
- E21B—EARTH DRILLING, e.g. DEEP DRILLING; OBTAINING OIL, GAS, WATER, SOLUBLE OR MELTABLE MATERIALS OR A SLURRY OF MINERALS FROM WELLS
- E21B44/00—Automatic control systems specially adapted for drilling operations, i.e. self-operating systems which function to carry out or modify a drilling operation without intervention of a human operator, e.g. computer-controlled drilling systems; Systems specially adapted for monitoring a plurality of drilling variables or conditions
- E21B44/02—Automatic control of the tool feed
-
- E—FIXED CONSTRUCTIONS
- E21—EARTH DRILLING; MINING
- E21B—EARTH DRILLING, e.g. DEEP DRILLING; OBTAINING OIL, GAS, WATER, SOLUBLE OR MELTABLE MATERIALS OR A SLURRY OF MINERALS FROM WELLS
- E21B44/00—Automatic control systems specially adapted for drilling operations, i.e. self-operating systems which function to carry out or modify a drilling operation without intervention of a human operator, e.g. computer-controlled drilling systems; Systems specially adapted for monitoring a plurality of drilling variables or conditions
- E21B44/02—Automatic control of the tool feed
- E21B44/06—Automatic control of the tool feed in response to the flow or pressure of the motive fluid of the drive
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T137/00—Fluid handling
- Y10T137/8593—Systems
- Y10T137/87096—Valves with separate, correlated, actuators
- Y10T137/87121—Coaxial stems
- Y10T137/87129—Rotary
- Y10T137/87137—And reciprocating
Description
Fremgangsmåte til fremstilling av salter, alkylerings- og acyleringsprodukter av "-formyl-/'-alkoksypropionitriler. Process for the preparation of salts, alkylation and acylation products of "-formyl-/'-alkoxypropionitrile.
Oppfinnelsen angår en fremgangsmåte The invention relates to a method
til fremstilling av salter, alkylerings- og for the production of salts, alkylation and
acyleringsprodukter av -formyl-alkoksypropionitriler av den alminnelige formel: acylation products of -formyl-alkoxypropionitriles of the general formula:
hvor R betegner en alkylgruppe og R, betegner metall, fortrinsvis alkalimetall, en where R denotes an alkyl group and R denotes metal, preferably alkali metal, a
alkyl- eller en acylgruppe. alkyl or an acyl group.
Disse stoffer er særlig godt skikket These substances are particularly well suited
som utgangsmateriale ved den syntetiske as starting material in the synthetic
fremstilling av 2-metyl-4-amino-5-alkok-sy-pyrimidin, som anvendes ved syntetise-ring av vitamin B,, idet de, for saltenes production of 2-methyl-4-amino-5-alkoxypyrimidine, which is used in the synthesis of vitamin B, since, for the salts
vedkommende etter alkylering eller acylering kan omsettes med acetamidin til dannelse av den nevnte pyrimidin. that person after alkylation or acylation can be reacted with acetamidine to form the aforementioned pyrimidine.
Ifølge oppfinnelsen fremstilles saltene ved omsetning av akrylnitril med en maursyreester i nærvær av et alkoholat. Så-fremt der ønskes fremstilt alkylerings- eller acyleringsprodukter av saltene, etter-følges den foran nevnte omsetning av en behandling med alkylerings- eller acyleringsmiddel, eventuelt uten forutgående isolasjon av saltene. According to the invention, the salts are prepared by reacting acrylonitrile with a formic acid ester in the presence of an alcoholate. If it is desired to produce alkylation or acylation products of the salts, the aforementioned reaction is followed by a treatment with an alkylating or acylating agent, possibly without prior isolation of the salts.
Omsettes akrylnitril f. eks. med etylformiat i nærvær av natriumetylat skjer omsetningen etter følgende reaksjons-skjema: Convert acrylonitrile, e.g. with ethyl formate in the presence of sodium ethylate, the reaction takes place according to the following reaction scheme:
Ved en etterfølgende alkylering med In a subsequent alkylation with
f. eks. dimetylsulfat omdannes natriumsaltet til a-metoksymetylen-p-etoksy-propio-nitril, mens det ved acylering, f. eks. med e.g. dimethylsulphate, the sodium salt is converted to α-methoxymethylene-p-ethoxy-propionitrile, while by acylation, e.g. with
acetylklorid, omdannes til a-acetoksyme-tylen-p-etoksypropionitril. acetyl chloride, is converted to α-acetoxymethylene-p-ethoxypropionitrile.
Det er ganske visst kjent å omsette en It is certainly known to trade one
akrylsyreester med en maursyreester i acrylic acid ester with a formic acid ester in it
nærvær av et alkoholat til dannelse av et presence of an alcoholate to form a
salt av en oc-formyl-(3-alkoksypropionsyre-ester, men et slikt salt er mindre hensikts-messig som utgangsmateriale ved fremstillingen av pyrimidindelen av vitamin B,, salt of an o-formyl-(3-alkoxypropionic acid ester), but such a salt is less suitable as a starting material in the preparation of the pyrimidine part of vitamin B,,
idet det ved reaksjon med acetamidin gir since upon reaction with acetamidine it gives
en 4-hydroksypyrimidin, hvor hydroksyl-gruppen etterpå skal omdannes til en a 4-hydroxypyrimidine, where the hydroxyl group must afterwards be converted to a
aminogruppe. amino group.
Videre er det kjent, at a-natriumfor-myl-p-etoksypropionitril kan fremstilles Furthermore, it is known that α-sodium formyl-p-ethoxypropionitrile can be prepared
av etoksypropionitril, etylformiat og metallisk natrium, idet etoksypropionitrilet først fremstilles ut fra etylencyanhydrin. of ethoxypropionitrile, ethyl formate and metallic sodium, the ethoxypropionitrile being first prepared from ethylene cyanohydrin.
Utbyttet ved denne kjente prosess er imidlertid betydelig lavere enn utbyttet ved prosessen ifølge oppfinnelsen, og anven-delsen av metallisk natrium krever spesiell apparatur og sikkerhetsforanstaltninger under arbeidet. The yield in this known process is, however, significantly lower than the yield in the process according to the invention, and the use of metallic sodium requires special equipment and safety measures during work.
Foreliggende oppfinnelse har videre den fordel at utgangsmaterialene er lettere tilgjengelige, og som nevnt ovenfor er det ikke ved fremstillingen av alkylerings- og acyleringsproduktene nødvendig å isolere saltet av «-formyl-p-alkoksypropionitril av reaksjonsblandingen, men denne kan umiddelbart omsettes med alkylerings- eller acyleringsmiddel, slik at også de derved vunne produkter fås i høyt utbytte. The present invention also has the advantage that the starting materials are more easily available, and as mentioned above, when preparing the alkylation and acylation products, it is not necessary to isolate the salt of "-formyl-p-alkoxypropionitrile from the reaction mixture, but this can be immediately reacted with alkylation or acylating agent, so that the products thus obtained are also obtained in high yield.
Til ytterligere belysning av oppfinnelsen tjener følgende utførelseseksempler: Eksempel 1: 680 g natriumetylat oppslemmes i 5 liter bensol eller toluol, og til oppslem-mingen tilsettes en blanding av 530 g akrylnitril og 900 g etylformiat. Ved henstand i romtemperatur dannes natriumsaltet av a-formyl-p-etoksypropionitril som eventuelt kan separeres. Fortrinsvis viderebehandles reaksjonsblandingen imidlertid umiddelbart med 1000 ml dimetylsulfat, idet tempe-raturen settes opp til omkring 60" C. Ved henstand utskilles der natriummetylsulfat, som frafiltreres og filtratet destilleres deretter i vakuum.En fraksjon, som avdestil-lerer mellom 85 og 110° C ved 3 mm kvikk-sølvtrykk tas ut. Den veier 750 g og består av a-metoksymetylen-(3-etoksypropionitril, hvis brytningsindeks n|)20° C er 1.4600. The following examples serve to further illustrate the invention: Example 1: 680 g of sodium ethylate are suspended in 5 liters of benzene or toluene, and a mixture of 530 g of acrylonitrile and 900 g of ethyl formate is added to the suspension. On standing at room temperature, the sodium salt of α-formyl-p-ethoxypropionitrile is formed, which can optionally be separated. Preferably, however, the reaction mixture is further treated immediately with 1000 ml of dimethylsulphate, the temperature being raised to around 60°C. On standing, sodium methylsulphate separates out, which is filtered off and the filtrate is then distilled in a vacuum. A fraction, which distills off between 85 and 110°C at 3 mm mercury pressure is taken out It weighs 750 g and consists of α-methoxymethylene-(3-ethoxypropionitrile), whose refractive index n|)20° C is 1.4600.
Eksempel 2: 108 g natriummetylat oppslemmes i 800 ml toluol, og der tilsettes ved 20—25° C en blanding av 106 g akrylnitril + 145 g metylformiat. Etter henstand til neste dag tilsettes 200 ml dimetylsulfat, og der opp-hetes til 60° C. Etter frafiltrering av det ut-skilte natriummetylsulfat destilleres filtratet i vakuum. Fraksjonen, hvis kokepunkt ved 3 mm Hg-trykk ligger mellom 85 og 95° C, består av a-metoksymetylen-p-metoksypropionitril. Example 2: 108 g of sodium methylate is suspended in 800 ml of toluene, and a mixture of 106 g of acrylonitrile + 145 g of methyl formate is added at 20-25° C. After standing until the next day, 200 ml of dimethylsulphate is added, and the mixture is heated to 60° C. After filtering off the separated sodium methylsulphate, the filtrate is distilled in a vacuum. The fraction, whose boiling point at 3 mm Hg pressure is between 85 and 95° C, consists of α-methoxymethylene-p-methoxypropionitrile.
Eksempel 3: Til en oppslemming av 68 g natrium etylat i 1 liter vannfri eter tilsettes dråpe- vis en blanding av 90 g etylformiat og 53 g akrylnitril. Blandingen står under omrø-ring i 12 timer ved romtemperatur, og det dannede natriumsalt av a-hydroksymetylen-p-etoksypropionitril suges deretter fra. Utbyttet er ca. 130 g. Example 3: For a slurry of 68 g of sodium ethylate in 1 liter of anhydrous ether is added dropwise show a mixture of 90 g of ethyl formate and 53 g of acrylonitrile. The mixture is stirred for 12 hours at room temperature, and the formed sodium salt of α-hydroxymethylene-p-ethoxypropionitrile is then sucked off. The yield is approx. 130 g.
Eksempel 4: 40 g natriumsalt av a-hydroksymetylen -(3-etoksypropionitril oppslemmes i 500 ml vannfri eter og der tilsettes 40 ml acetylklorid. Etter avsugning av natriumklorid fraksjoneres reaksjonsblandingen i vakuum. Fraksjonen, hvis kokepunkt ved 10 mm Hg-trykk er 128—130" C består av a-acetoksymetylen-(3-.etoksypropionitril som har en brytningsindeks 111,20° C = 1.462. Example 4: 40 g of the sodium salt of α-hydroxymethylene-(3-ethoxypropionitrile) is suspended in 500 ml of anhydrous ether and 40 ml of acetyl chloride is added there. After suctioning off the sodium chloride, the reaction mixture is fractionated in vacuum. The fraction, whose boiling point at 10 mm Hg pressure is 128— 130" C consists of α-acetoxymethylene-(3-ethoxypropionitrile) which has a refractive index of 111.20° C = 1,462.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE12377/64A SE301939B (en) | 1964-10-14 | 1964-10-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO116185B true NO116185B (en) | 1969-02-10 |
Family
ID=20295640
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO159992A NO116185B (en) | 1964-10-14 | 1965-10-08 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3381761A (en) |
| CH (1) | CH470574A (en) |
| DE (1) | DE1458635C3 (en) |
| FI (1) | FI43976C (en) |
| GB (1) | GB1056369A (en) |
| NO (1) | NO116185B (en) |
| SE (1) | SE301939B (en) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3561542A (en) * | 1969-03-20 | 1971-02-09 | Gardner Denver Co | Control system for rock drills |
| US3669197A (en) * | 1969-03-20 | 1972-06-13 | Gardner Denver Co | Control system for rock drills |
| FI55892C (en) * | 1974-03-18 | 1979-10-10 | Tampella Oy Ab | HYDRAULISK BORRMASKIN I SYNNERHET BERGBORRNINGSMASKIN |
| US4368918A (en) * | 1980-01-23 | 1983-01-18 | Voest-Alpine Aktiengesellschaft | Process and apparatus for controlling the water supply to the cutting head of a cutting machine |
| AU784583B2 (en) * | 2001-07-14 | 2006-05-04 | Hilti Aktiengesellschaft | Support for supporting a power tool on a displacement carriage |
| FI20012407A (en) * | 2001-12-05 | 2003-06-06 | Sandvik Tamrock Oy | Input bar and hydraulic element |
| US8261855B2 (en) * | 2009-11-11 | 2012-09-11 | Flanders Electric, Ltd. | Methods and systems for drilling boreholes |
| CN102410010B (en) * | 2011-11-22 | 2015-07-08 | 北京市三一重机有限公司 | Rotary drilling rig and main winding floating system thereof |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3273595A (en) * | 1966-09-20 | Novak gas plow control valve | ||
| US2806448A (en) * | 1955-10-24 | 1957-09-17 | Joy Mfg Co | Control for rock drills |
| GB983141A (en) * | 1960-06-10 | 1965-02-10 | Plessey Co Ltd | Improvements in or relating to fuel control in internal-combustion turbine engines |
| US3191692A (en) * | 1961-11-20 | 1965-06-29 | Atlas Copco Ab | Back head of pneumatic tools |
| US3204706A (en) * | 1962-11-07 | 1965-09-07 | Atlas Copco Ab | Automatic feeding device for rock drills |
| US3307637A (en) * | 1964-06-23 | 1967-03-07 | Atlas Copco Ab | Automated rock drill positioning support |
-
1964
- 1964-10-14 SE SE12377/64A patent/SE301939B/xx unknown
-
1965
- 1965-10-08 NO NO159992A patent/NO116185B/no unknown
- 1965-10-12 GB GB43208/65A patent/GB1056369A/en not_active Expired
- 1965-10-13 FI FI652446A patent/FI43976C/en active
- 1965-10-13 US US495450A patent/US3381761A/en not_active Expired - Lifetime
- 1965-10-13 DE DE1458635A patent/DE1458635C3/en not_active Expired
- 1965-10-14 CH CH1417665A patent/CH470574A/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| FI43976B (en) | 1971-04-30 |
| CH470574A (en) | 1969-03-31 |
| FI43976C (en) | 1971-08-10 |
| GB1056369A (en) | 1967-01-25 |
| DE1458635C3 (en) | 1978-07-13 |
| DE1458635A1 (en) | 1970-01-08 |
| SE301939B (en) | 1968-07-01 |
| DE1458635B2 (en) | 1974-02-14 |
| US3381761A (en) | 1968-05-07 |
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