Dichloromethane → HCID 13457850, compound

HRID 463542Notes

Reaction equation

HRID 463542 reaction equation
C(Cl)Cl.[SH:4][C:5]1[N:9]([CH3:10])[C:8]2[CH:11]=[CH:12][CH:13]=[CH:14][C:7]=2[N:6]=1.Br[CH:16]([C:20]1[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=1)[C:17]([OH:19])=[O:18]>C(N(CC)CC)C>[Cl:26][C:23]1[CH:22]=[CH:21][C:20]([CH:16]([S:4][C:5]2[N:9]([CH3:10])[C:8]3[CH:11]=[CH:12][CH:13]=[CH:14][C:7]=3[N:6]=2)[C:17]([OH:19])=[O:18])=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 10490868alpha-Bromo-4-chlorophenylacetic acidHCID 178481665HCID 178481665, compound

Product 1

HCID 13457850HCID 13457850, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A methylene chloride solution of 3.3 g (0.02M) of 2-mercapto-1-methyl-1H-benzimidazole, 5.0 g (0.02M) of α-bromo-(p-chlorophenyl)acetic acid and 4.0 g (0.04M) of triethylamine is heated to reflux overnight. The reaction mixture is neutralized with a diluted HCL solution. The layers are separated and the organic layer is dried over anhydrous magnesium sulfate. After removal of methylene chloride the residue is recrystallized from acetonitrile. The recrystallized material weighs 4.1 g (41% yield) and has a melting point of 161°-3° C. dec.

Workup

  1. temperatureto reflux overnight
  2. customThe layers are separated
  3. dry with materialthe organic layer is dried over anhydrous magnesium sulfate
  4. customAfter removal of methylene chloride the residue
  5. customis recrystallized from acetonitrile

Sources & evidence

ORD record
ord-d0ca4776a20d40edbe0eb7f5c3e47d45
Source dataset
uspto-grants-1985_05
Patent number
US04520196

Reaction notes

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