Guanidine → Trimethoprim

HRID 614282

반응식

HRID 614282 반응식
C([C:6]([CH:22](OCC)OCC)([CH2:9][C:10]1[CH:15]=[C:14]([O:16][CH3:17])[C:13]([O:18][CH3:19])=[C:12]([O:20][CH3:21])[CH:11]=1)[C:7]#[N:8])(OCC)=O.[OH-].[K+].[NH2:31][C:32]([NH2:34])=[NH:33]>C(O)C>[NH2:34][C:32]1[N:33]=[C:7]([NH2:8])[C:6]([CH2:9][C:10]2[CH:15]=[C:14]([O:16][CH3:17])[C:13]([O:18][CH3:19])=[C:12]([O:20][CH3:21])[CH:11]=2)=[CH:22][N:31]=1

참가 물질

5

반응물 3

HCID 3520GuanidineHCID 14797Potassium HydroxideHCID 12559126alpha-Carbethoxy-alpha-diethoxymethyl-beta-(3,4,5-trimethoxyphenyl)propionitrile

생성물 1

HCID 5578Trimethoprim

시약·촉매·용매 1

HCID 702Ethanol용매3회

실험 절차

A solution of α-carbethoxy-α-diethoxymethyl-β-(3,4,5-trimethoxyphenyl)propionitrile (7.9 g, 0.02 mol) and an equivalent amount of potassium hydroxide in ethanol (50 ml) was heated at reflux for one hour. A solution of guanidine (0.07 mol) in ethanol (50 ml) was added, and reflux was resumed. Some ethanol was allowed to boil off bringing the reaction temperature up to 85°. After about 20 hours at reflux the mixture was allowed to cool, and the product was filtered and washed with ethanol. The crude product was purified by treating with hot aqueous acetic acid and reprecipitation with ammonium hydroxide. The yield of purified trimethoprim (m.p. 197°-198°) was 3.6g (62%), its identity being confirmed by an NMR spectrum.

후처리

  1. temperatureat reflux for one hour
  2. temperaturereflux
  3. customup to 85°
  4. temperatureAfter about 20 hours at reflux the mixture
  5. temperatureto cool
  6. filtrationthe product was filtered
  7. washwashed with ethanol
  8. customThe crude product was purified
  9. additionby treating with hot aqueous acetic acid and reprecipitation with ammonium hydroxide

출처 및 근거

ORD 기록
ord-e6a093a3d9a8427bba9ef92b52d464cf
출처 데이터셋
uspto-grants-1979_03
특허 번호
US04144263

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