Water → Methyl 4-[((3-methylbutyl){4-[4-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl}amino)methyl]benzoate

HRID 507998

반응식

HRID 507998 반응식
[CH3:1][CH:2]([CH3:21])[CH2:3][CH2:4][NH:5][C:6]1[S:7][CH:8]=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)[N:10]=1.[H-].[Na+].Br[CH2:25][C:26]1[CH:35]=[CH:34][C:29]([C:30]([O:32][CH3:33])=[O:31])=[CH:28][CH:27]=1.O>CN(C)C=O>[CH3:1][CH:2]([CH3:21])[CH2:3][CH2:4][N:5]([CH2:25][C:26]1[CH:35]=[CH:34][C:29]([C:30]([O:32][CH3:33])=[O:31])=[CH:28][CH:27]=1)[C:6]1[S:7][CH:8]=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:18])([F:20])[F:19])=[CH:13][CH:12]=2)[N:10]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 24758Sodium hydrideHCID 256687Methyl 4-(bromomethyl)benzoateHCID 23143261N-(3-Methylbutyl)-4-[4-(trifluoromethyl)phenyl]-1,3-thiazol-2-amine

생성물 1

HCID 23157327Methyl 4-[((3-methylbutyl){4-[4-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl}amino)methyl]benzoate수율 76%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of N-(3-methylbutyl)-4-[4-(trifluoromethyl)phenyl]-1,3-thiazole-2-amine (1.20 g, 3.82 mmol) in N,N-dimethylformamide (20 mL) was added sodium hydride (60% in oil, 229 mg, 5.73 mmol) and the mixture was stirred for 30 min. Methyl 4-(bromomethyl)benzoate (1.05 g, 4.58 mmol) was added and the mixture was stirred at 60° C. for 1.5 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=97/3-hexane/ethyl acetate=60/40) to give the title compound (1.34 g, yield 76%) as a yellow oil.

후처리

  1. stirringthe mixture was stirred at 60° C. for 1.5 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=97/3-hexane/ethyl acetate=60/40)

출처 및 근거

ORD 기록
ord-d55de63954cf499ea2b2c96a9baf759f
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07786165B2

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