Water → Methyl 4-[[(2-phenylethyl)(4-phenyl-1,3-thiazol-2-yl)amino]methyl]benzoate

HRID 507910노트

반응식

HRID 507910 반응식
[C:1]1([C:7]2[N:8]=[C:9]([NH:12][CH2:13][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[S:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Br[CH2:24][C:25]1[CH:34]=[CH:33][C:28]([C:29]([O:31][CH3:32])=[O:30])=[CH:27][CH:26]=1.O>CN(C)C=O>[C:15]1([CH2:14][CH2:13][N:12]([CH2:24][C:25]2[CH:34]=[CH:33][C:28]([C:29]([O:31][CH3:32])=[O:30])=[CH:27][CH:26]=2)[C:9]2[S:10][CH:11]=[C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[N:8]=2)[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 24758Sodium hydrideHCID 543394-Phenyl-N-(2-phenylethyl)-2-thiazolamineHCID 256687Methyl 4-(bromomethyl)benzoate

생성물 1

HCID 23111810Methyl 4-[[(2-phenylethyl)(4-phenyl-1,3-thiazol-2-yl)amino]methyl]benzoate수율 48%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 4-phenyl-N-(2-phenylethyl)-1,3-thiazole-2-amine (4.63 g, 16.5 mmol) in N,N-dimethylformamide (50 mL) was added sodium hydride (60% in oil, 990 mg, 24.8 mmol) and the mixture was stirred for 30 min. Methyl 4-(bromomethyl)benzoate (4.54 g, 19.8 mmol) was added and the mixture was stirred at room temperature for 2 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with water, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (5%-50% ethyl acetate/hexane) to give the title compound (3.39 g, yield 48%) as a yellow oil.

후처리

  1. stirringthe mixture was stirred at room temperature for 2 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with water
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (5%-50% ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-af6a9c70612f43b19eb5e9f02603a47f
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07786165B2

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