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

HRID 2389467ノート

反応式

HRID 2389467 の反応式
[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]

参加物

5

反応物 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 178451223HCID 178451223、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-635a7e5742a742b8b1c74a346c6a942a
出典データセット
uspto-grants-2012_09
特許番号
US08273740B2

反応ノート

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