Acetaldehyde → HCID 178463263, 화합물

HRID 1595403노트

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HRID 1595403 반응식
[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]

참가 물질

8

반응물 5

HCID 177AcetaldehydeHCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 178489037HCID 178489037, 화합물

생성물 1

HCID 178463263HCID 178463263, 화합물

시약·촉매·용매 2

HCID 887Methanol용매HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-0c6e2a002de14539be3eebf7392967fc
출처 데이터셋
uspto-grants-2001_09
특허 번호
US06288061B1

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