Methyl 4-(bromomethyl)benzoate → 4-(6-Methoxy-1H-benzoimidazol-2-ylsulfanylmethyl)-benzoic acid methyl ester hydrobromide

HRID 2182458Notes

Reaction equation

HRID 2182458 reaction equation
[Br:1][CH2:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=1.[CH3:13][O:14][C:15]1[CH:24]=[CH:23][C:18]2[N:19]=[C:20]([SH:22])[NH:21][C:17]=2[CH:16]=1>CN(C=O)C>[BrH:1].[CH3:10][O:9][C:7](=[O:8])[C:6]1[CH:11]=[CH:12][C:3]([CH2:2][S:22][C:20]2[NH:21][C:17]3[CH:16]=[C:15]([O:14][CH3:13])[CH:24]=[CH:23][C:18]=3[N:19]=2)=[CH:4][CH:5]=1

Participants

4

Reactant 2

HCID 256687Methyl 4-(bromomethyl)benzoateHCID 178488032HCID 178488032, compound

Product 1

HCID 668939074-(6-Methoxy-1H-benzoimidazol-2-ylsulfanylmethyl)-benzoic acid methyl ester hydrobromideYield 91.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of methyl 4-(bromomethyl)benzoate (2.51 g, 11.0 mmol) in DMF (50 mL) was added 5-methoxy-2benzimidazolethiol (1.98 g, 11.0 mmol). The mixture was stirred at room temperature for 24 h and the solvent was evaporated in vacuo. The residue was suspended in ethyl acetate and the hydrobromide salt was collected by filtration to afford the title compound 234 (4.10 g, 91% yield) as a colorless solid. 1H NMR: (DMSO-d6) δ (ppm): 7.90 (d, J=8.2 Hz, 2H), 7.55 (d, J=8.2 Hz, 2H), 7.45 (d, J=8.2 Hz, 1H), 7.03 (s,1H), 6.94 (d, J=8.2 Hz,1H), 4.65 (s,2H), 3.82 (s,3H), 3.79 (s, 3H).

Workup

  1. customthe solvent was evaporated in vacuo
  2. filtrationthe hydrobromide salt was collected by filtration

Sources & evidence

ORD record
ord-2a6741a313874eeb9eebdbc1189efa18
Source dataset
uspto-grants-2005_05
Patent number
US06897220B2

Reaction notes

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