Guanidine → Trimethoprim

HRID 614282

反応式

HRID 614282 の反応式
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

参加物

5

反応物 3

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

生成物 1

HCID 5578Trimethoprim

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒3 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-e6a093a3d9a8427bba9ef92b52d464cf
出典データセット
uspto-grants-1979_03
特許番号
US04144263

関連ノート

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