Potassium Carbonate → Tert-butyl [2-(2-phenoxy-ethylsulfanyl)-benzoimidazol-1-yl]-acetate

HRID 2389471Notes

Reaction equation

HRID 2389471 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][CH2:21][O:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C([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][CH2:20][CH2:21][O:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([CH3:13])([CH3:14])[CH3:12]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 68526Benzene, (2-bromoethoxy)-HCID 178451223HCID 178451223, compound

Product 1

HCID 125506678Tert-butyl [2-(2-phenoxy-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, 53 mg, 0.2 mmol), 1-(2-bromo-ethoxy)-benzene (48.3 mg, 0.22 mmol) and K2CO3 (41.4 mg, 0.3 mmol) in acetone (0.8 ml) is refluxed for 3 h. The suspension is cooled to rt and filtered through a short pad of silica-gel. The volatiles are removed in vacuo and the residue is dried under high vacuum affording the title compound as a colourless oil. This material was used in the next step without further purification: tR=2.55 min (LC-2), MS (pos.): m/z 385.2 [M+H]+; 1H NMR (CDCl3): δ (ppm) 1.48 (s, 9H, tBu), 3.96 (m, 2H, SCH2), 4.48 (t, 2H, OCH2), 4.90 (s, 2H, CH2CO2), 6.90 (d, 2Harom), 7.24-7.38 (m, 5Harom), 7.86 (m, 1Harom).

Workup

  1. temperatureis refluxed for 3 h
  2. filtrationfiltered through a short pad of silica-gel
  3. customThe volatiles are removed in vacuo
  4. customthe residue is dried under high vacuum

Sources & evidence

ORD record
ord-48149d94441b41f09287c3c3740e47e6
Source dataset
uspto-grants-2012_09
Patent number
US08273740B2

Reaction notes

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