Triethylamine → alpha-[(5-Chloro-1-methylbenzimidazol-2-yl)thio]benzeneacetic acid

HRID 463545Notes

Reaction equation

HRID 463545 reaction equation
[Cl:1][C:2]1[CH:12]=[CH:11][C:5]2[N:6]([CH3:10])[C:7]([SH:9])=[N:8][C:4]=2[CH:3]=1.Br[CH:14]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:15]([OH:17])=[O:16].C(N(CC)CC)C>C(Cl)Cl>[Cl:1][C:2]1[CH:12]=[CH:11][C:5]2[N:6]([CH3:10])[C:7]([S:9][CH:14]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:15]([OH:17])=[O:16])=[N:8][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 97919Bromo(phenyl)acetic acidHCID 1784816675-chloro-1-methyl-1H-benzo[d]imidazole-2-thiol

Product 1

HCID 13457846alpha-[(5-Chloro-1-methylbenzimidazol-2-yl)thio]benzeneacetic acidYield 775.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5.96 g (0.03M) of 5-Chloro-2-mercapto-1-methylbenzimidazole of C above, 0.5 g (0.03M) of α-bromophenylacetic acid and 6.0 g (0.06M) of triethylamine are dissolved in methylene chloride (200 ml) and the mixture heated to reflux overnight. The basic solution is washed with a diluted HCl solution and a white solid is collected. The crude material is recrystallized from 5 L of acetonitrile to give 6.0 g (60% yield) of the title compound, m.p. 203°-5° C. dec.

Workup

  1. temperaturethe mixture heated
  2. temperatureto reflux overnight
  3. washThe basic solution is washed with a diluted HCl solution
  4. customa white solid is collected
  5. customThe crude material is recrystallized from 5 L of acetonitrile

Sources & evidence

ORD record
ord-31ee51b17b7b40209f4361fbc3827e69
Source dataset
uspto-grants-1985_05
Patent number
US04520196

Reaction notes

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