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

HRID 2389467Notes

Reaction equation

HRID 2389467 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-635a7e5742a742b8b1c74a346c6a942a
Source dataset
uspto-grants-2012_09
Patent number
US08273740B2

Reaction notes

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