Acetaldehyde → HCID 178463263、化合物

HRID 1595403ノート

反応式

HRID 1595403 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:9][C:10]([C:21]3[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=3)=[C:11]([C:13]([NH:15][C:16]3[S:17][CH:18]=[CH:19][N:20]=3)=[O:14])[N:12]=2)=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[CH:34](=O)[CH3:35].[BH4-].[Na+].C(=O)([O-])O.[Na+]>O1CCCC1.CO>[CH2:34]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:9][C:10]([C:21]3[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=3)=[C:11]([C:13]([NH:15][C:16]3[S:17][CH:18]=[CH:19][N:20]=3)=[O:14])[N:12]=2)=[CH:4][CH:3]=1)[CH3:35]

参加物

8

反応物 5

HCID 177AcetaldehydeHCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 178489037HCID 178489037、化合物

生成物 1

HCID 178463263HCID 178463263、化合物

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

2-(4-Aminophenyl)-5-(4-methoxyphenyl)-N-(2-thiazolyl)-imidazole-4-carboxamide (1.0 g) obtained in Example 48 was dissolved in a mixed solvent of tetrahydrofuran and methanol, and added to a solution of 4N sulfuric acid (0.2 ml) and acetaldehyde (0.2 ml) in tetrahydrofuran. To the solution was added sodium borohydride (0.13 g) and the mixture was stirred at room temperature for 2 hr. To the reaction mixture was added a saturated aqueous sodium hydrogencarbonate solution and the mixture was extracted with ethyl acetate. The ethyl acetate phase was washed with saturated brine, dried and concentrated. The residue was purified by silica gel chromatography using, as a mobile phase, chloroform/ethyl acetate=100:1 to give 2-(4-ethylaminophenyl)-5-(4-methoxyphenyl)-N-(2-thiazolyl)imidazole-4-carboxamide (1.2 g). This was converted to hydrochloride to give 2-(4-ethylaminophenyl)-5-(4-methoxy-phenyl)-N-(2-thiazolyl)imidazole-4-carboxamide hydrochloride (0.48 g), melting point 250° C. or above.

後処理

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate phase was washed with saturated brine
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel chromatography

出典と根拠

ORDレコード
ord-0c6e2a002de14539be3eebf7392967fc
出典データセット
uspto-grants-2001_09
特許番号
US06288061B1

反応ノート

読み込み中…