Potassium Carbonate → 4-[(1H-1,3-benzodiazol-2-ylsulfanyl)methyl]benzoic acid

HRID 34671

Reaction equation

HRID 34671 reaction equation
[SH:1][C:2]1[NH:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]([OH:27])=[O:26])=[CH:21][CH:20]=1>CN(C=O)C>[C:25]([C:22]1[CH:23]=[CH:24][C:19]([CH2:18][S:1][C:2]2[NH:3][C:4]3[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=3[N:6]=2)=[CH:20][CH:21]=1)([OH:27])=[O:26]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 225994-(Bromomethyl)benzoic acidHCID 178527775HCID 178527775, compound

Product 1

HCID 49921594-[(1H-1,3-benzodiazol-2-ylsulfanyl)methyl]benzoic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

4.6 g (30 mmol) of 2-mercaptobenzimidazole were initially introduced into 60 ml of dry DMF, 8.3 g (60 mmol) of K2CO3 were added, and a solution of 6.7 g (31 mmol) of α-bromo-4-toluic acid in 15 ml of dry DMF was added dropwise at room temperature. After 4 hours, a solid residue was filtered off with suction, the DMF was removed in vacuo, and the residue was taken up in aqueous hydrochloric acid at pH 2. Crystals of the title compound separated out, and these were washed with water, methanol and ether and dried.

Workup

  1. additionwere added
  2. filtrationa solid residue was filtered off with suction
  3. customthe DMF was removed in vacuo
  4. customCrystals of the title compound separated out
  5. washthese were washed with water, methanol and ether
  6. customdried

Sources & evidence

ORD record
ord-934a558e455a4a6d9a5a76c76274324d
Source dataset
uspto-grants-1988_08
Patent number
US04762848

Linked notes

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