Methanol → HCID 178473123, compound

HRID 2183564Notes

Reaction equation

HRID 2183564 reaction equation
[SH:1][C:2]1[NH:3][C:4]2[CH:10]=[C:9](C)[CH:8]=[CH:7][C:5]=2[N:6]=1.Br[CH2:13][C:14](=[O:20])[C:15]([O:17][CH2:18][CH3:19])=[O:16].[CH3:21][OH:22]>CC(C)=O>[CH2:18]([O:17][C:15](=[O:16])[C:14](=[O:20])[CH2:13][S:1][C:2]1[NH:6][C:5]2[CH:7]=[CH:8][C:9]([O:22][CH3:21])=[CH:10][C:4]=2[N:3]=1)[CH3:19]

Participants

5

Reactant 3

HCID 887MethanolHCID 66144Ethyl bromopyruvateHCID 178423448HCID 178423448, compound

Product 1

HCID 178473123HCID 178473123, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 2-mercapto-5-methylbenzimidazole (200 mg, 1.22 mmol) and ethyl 3-bromopyruvate (0.20 mL, 1.43 mmol) in methanol (2 mL) and acetone (3 mL) was shaken at room temperature for 4 hours. The solvents were removed under the reduced pressure on a rotary evaporator. The residue was triturated with ethyl acetate. Solvent was decanted and the residue was dissolved in methylene chloride. The solution was washed with diluted aqueous sodium bicarbonate solution and water, and then dried over magnesium sulfate. Removal of the solvent gave the expected product, 3-(5-methoxy-1H-benzoimidazol-2-ylsulfanyl)-2-oxo-propionic acid ethyl ester (300 mg, 88%). 1H-NMR (D3COD, 300 MHz) δ (ppm): 7.19 (br. s, 1H), 7.10 and 7.04 (br. 2 s, 1H), 6.94 (d, J=8.2 Hz, 1H), 4.34 (q, J=7.1 Hz, 2H), 4.31 (br. s, 1H), 3.91 (br. s, 1H), 2.37 (br. s, 3H), 1.26 (t, J=7.1 Hz, 3H). MS (ESI): m/z 279 (M+1, 100).

Workup

  1. customThe solvents were removed under the reduced pressure on a rotary evaporator
  2. customThe residue was triturated with ethyl acetate
  3. customSolvent was decanted
  4. dissolutionthe residue was dissolved in methylene chloride
  5. washThe solution was washed with diluted aqueous sodium bicarbonate solution and water
  6. dry with materialdried over magnesium sulfate
  7. customRemoval of the solvent

Sources & evidence

ORD record
ord-a32e1a5e9e1640d6bc3d18ad6ddb12c7
Source dataset
uspto-grants-2005_05
Patent number
US06900218B2

Reaction notes

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