Benzyl Bromide → Tert-butyl[2-(1-phenyl-ethylsulfanyl)-benzoimidazol-1-yl]-acetate

HRID 2389467노트

반응식

HRID 2389467 반응식
[SH:1][C:2]1[N:6]([CH2:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[C:5]2[CH:15]=[CH:16][CH:17]=[CH:18][C:4]=2[N:3]=1.Br[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[C:27]([O-])([O-])=O.[K+].[K+]>CC(C)=O>[C:11]([O:10][C:8](=[O:9])[CH2:7][N:6]1[C:5]2[CH:15]=[CH:16][CH:17]=[CH:18][C:4]=2[N:3]=[C:2]1[S:1][CH:20]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH3:27])([CH3:13])([CH3:14])[CH3:12]

참가 물질

5

반응물 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 178451223HCID 178451223, 화합물

생성물 1

HCID 90738283Tert-butyl[2-(1-phenyl-ethylsulfanyl)-benzoimidazol-1-yl]-acetate

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

A mixture of tert-butyl (2-mercapto-benzoimidazol-1-yl)-acetate (Intermediate 3-I, 50 mg, 0.19 mmol), 1-bromomethyl-benzene (38.5 mg, 28.5 μl, 0.2 mmol) and K2CO3 (52 mg, 0.38 mmol) in acetone (3 ml) is stirred at reflux overnight. The suspension is cooled to rt and filtered through Celite. Evaporation of the solvent in vacuo and drying under high vacuum yields quantitatively the title compound as a slightly yellow oil. This material is used in the next step without further purification. tR=7.45 min (LC-1), MS (pos.): m/z 369.21 [M+H]+; 1H-NMR (DMSO-d6): δ (ppm) 1.36 (s, 9H, tBu), 1.73 (d, 3H, Me), 4.94 (m, 2H, CH2CO2), 5.09 (q, 1H, SCHMePH), 7.16-7.20 (m, 2Harom), 7.26-7.36 (m, 3Harom), 7.44-7.50 (m, 3Harom), 7.61 (m, 1Harom).

후처리

  1. temperatureat reflux overnight
  2. filtrationfiltered through Celite
  3. customEvaporation of the solvent in vacuo
  4. customdrying under high vacuum

출처 및 근거

ORD 기록
ord-635a7e5742a742b8b1c74a346c6a942a
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08273740B2

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