Guanidine → Trimethoprim

HRID 614280

反応式

HRID 614280 の反応式
C(OC(OCC)[C:5]([CH:21]=O)([CH2:8][C:9]1[CH:14]=[C:13]([O:15][CH3:16])[C:12]([O:17][CH3:18])=[C:11]([O:19][CH3:20])[CH:10]=1)[C:6]#[N:7])C.[NH2:26][C:27]([NH2:29])=[NH:28]>C(O)C>[NH2:29][C:27]1[N:28]=[C:6]([NH2:7])[C:5]([CH2:8][C:9]2[CH:14]=[C:13]([O:15][CH3:16])[C:12]([O:17][CH3:18])=[C:11]([O:19][CH3:20])[CH:10]=2)=[CH:21][N:26]=1

参加物

4

反応物 2

HCID 3520GuanidineHCID 12559125alpha-Diethoxymethyl-alpha-formyl-beta-(3,4,5-trimethoxyphenyl) propionitrile

生成物 1

HCID 5578Trimethoprim収率 67.2%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

α-Diethoxymethyl-α-formyl-β-(3,4,5-trimethoxyphenyl) propionitrile (35.1 g, 0.10 mol) was added to an ethanolic solution of guanidine (from 0.35 mol of guanidine hydrochloride). The mixture was heated at reflux for a total of 6.5 hours during which time enough ethanol was allowed to boil off to bring the reaction temperature up to 85°. The dark solution was allowed to cool and stand overnight. The mixture was filtered, and the solid was washed with cold ethanol and dried to yield crude product (24.4 g, 84.1%). Purification was effected by dissolving the crude product in hot aqueous acetic acid and reprecipitation with concentrated ammonium hydroxide. The precipitate was washed twice with water, once with cold acetone, and dried to yield 2,4-diamino-5-(3,4,5-trimethoxybenzyl)pyrimidine (19.5 g, 67.2%), m.p. 197°-198° C. (identity confirmed by nmr). The acetone was concentrated in vacuo to dryness yielding additional though somewhat less pure trimethoprim (2,5 g, 8.6%, m.p. 194°-196° C.).

後処理

  1. temperatureThe mixture was heated
  2. customup to 85°
  3. temperatureto cool
  4. filtrationThe mixture was filtered
  5. washthe solid was washed with cold ethanol
  6. customdried
  7. customto yield crude product (24.4 g, 84.1%)
  8. customPurification
  9. dissolutionby dissolving
  10. customthe crude product in hot aqueous acetic acid and reprecipitation with concentrated ammonium hydroxide
  11. washThe precipitate was washed twice with water, once with cold acetone
  12. customdried

出典と根拠

ORDレコード
ord-ed68d8e212dc4b5499be1cf8e5adaa6b
出典データセット
uspto-grants-1979_03
特許番号
US04144263

関連ノート

読み込み中…