Methyl 4-(bromomethyl)benzoate → HCID 667702, compound

HRID 2292650Notes

Reaction equation

HRID 2292650 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[SH:10].[CH3:11][O:12][C:13](=[O:22])[C:14]1[CH:19]=[CH:18][C:17]([CH2:20]Br)=[CH:16][CH:15]=1>CO>[CH3:11][O:12][C:13](=[O:22])[C:14]1[CH:19]=[CH:18][C:17]([CH2:20][S:10][C:2]2[NH:3][C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[N:1]=2)=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 256687Methyl 4-(bromomethyl)benzoateHCID 178527775HCID 178527775, compound

Product 1

HCID 667702HCID 667702, compoundYield 60.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1H-Benzoimidazol-2-thiol (1.5 g, 0.01 mol) and 4-bromomethyl benzoic acid methyl ester (2.29 g; 0.01 mol) were heated at reflux in methanol (100 mL) for a period of 24 hours. The solvent was evaporated. The residue was dissolved in ethyl acetate and washed with saturated sodium bicarbonate solution, then with water. The organic phase was evaporated. The residue was dissolved in methanol. The resulting solution was saturated with hydrogen chloride. The solution was then concentrated to the precipitation point. The solid was collected and dried to give (1.8 g, 54% yield) of the title compound as a mono-hydrochloride, white solid, m.p. 229°-231° C. Anal. Calcd. for C16H14N2 O2S.HCl: C, 57.40; H, 4.52; N, 8.37. Found: C, 57.54; H, 4.47; N, 8.36. Mass spectrum (EI; M+) m/z 298. 1H-NMR (DMSO-d6 ; 400 MHz) δ 7.89 (d, 2H0, 7.62-7.65 (m, 4H); 7.39 (m, 2H), 4.89 (s, 2H), and 3.81 (s, 3H).

Workup

  1. customThe solvent was evaporated
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed with saturated sodium bicarbonate solution
  4. customThe organic phase was evaporated
  5. dissolutionThe residue was dissolved in methanol
  6. concentrationThe solution was then concentrated to the precipitation point
  7. customThe solid was collected
  8. customdried

Sources & evidence

ORD record
ord-1e686187f4374416b985b1a0f2c398b8
Source dataset
uspto-grants-1997_11
Patent number
US05684030

Reaction notes

Loading…