Potassium Carbonate → Tert-butyl[2-(2-methoxy-benzylsulfanyl)-benzoimidazol-1-yl]-acetate

HRID 2389469Notes

Reaction equation

HRID 2389469 reaction equation
C([O-])([O-])=O.[K+].[K+].[SH:7][C:8]1[N:12]([CH2:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C:11]2[CH:21]=[CH:22][CH:23]=[CH:24][C:10]=2[N:9]=1.[CH3:25][O:26][C:27]1[CH:34]=[CH:33][CH:32]=[CH:31][C:28]=1[CH2:29]Cl>CC(C)=O>[C:17]([O:16][C:14](=[O:15])[CH2:13][N:12]1[C:11]2[CH:21]=[CH:22][CH:23]=[CH:24][C:10]=2[N:9]=[C:8]1[S:7][CH2:29][C:28]1[CH:31]=[CH:32][CH:33]=[CH:34][C:27]=1[O:26][CH3:25])([CH3:19])([CH3:20])[CH3:18]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 814952-(Chloromethyl)anisoleHCID 178451223HCID 178451223, compound

Product 1

HCID 90907082Tert-butyl[2-(2-methoxy-benzylsulfanyl)-benzoimidazol-1-yl]-acetateYield 63.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A suspension of K2CO3 (31.4 mg, 0.23 mmol) in acetone (3 ml) containing tert-butyl (2-mercapto-benzoimidazol-1-yl)-acetate (Intermediate 3-I, 30 mg, 0.11 mmol) and 2-methoxybenzyl chloride (17.8 mg, 15.8 μl, 0.11 mmol) is stirred at rt overnight. Filtration over Celite and evaporation of the solvent in vacuo affords the pure title compound (27 mg) in 62% yield as a yellow oil: tR=7.47 min (LC-1), MS (pos.): m/z 385.20 [M+H]+; 1H NMR (DMSO-d6): δ (ppm) 1.37 (s, 9H, tBu), 3.90 (s, 3H, OCH3), 4.53 (s, 2H, SCH2), 4.92 (s, 2H, CH2CO2), 6.87 (t, 1Harom), 7.03 (d, 1Harom), 7.21 (m, 2Harom), 7.28 (t, 1Harom), 7.40 (d, 1Harom), 7.50 (m, 1Harom), 7.64 (m, 1Harom).

Workup

  1. filtrationFiltration
  2. customover Celite and evaporation of the solvent in vacuo

Sources & evidence

ORD record
ord-086a1f7b873e419c8bfdb9b685b6f8f0
Source dataset
uspto-grants-2012_09
Patent number
US08273740B2

Reaction notes

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