Hydrochloric Acid → ST50143142

HRID 248423Notes

Reaction equation

HRID 248423 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.Cl[CH2:12][C:13](=[O:15])[CH3:14].Cl.C([O-])(=O)C.[Na+]>O.CC(=O)CC>[C:13]([CH2:14][S:1][C:2]1[NH:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1)(=[O:15])[CH3:12]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6571ChloroacetoneHCID 517045Sodium AcetateHCID 178527775HCID 178527775, compound

Product 1

HCID 963486ST50143142

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6569Methyl Ethyl KetoneSolvent

Procedure

2-Mercaptobenzimidazole (14.6 g, 0.1 mole) and chloroacetone (9.25 g, 0.1 mole) were added to 2-butanone (400 ml) and refluxed for 5 hrs. On cooling the product hydrochloride, 21.24 g, 88% was isolated by filtration, washed with acetone and air dried. The salt was dissolved in water (150 ml) and added to a solution of sodium acetate (7.2 g, 0.088 mole) in water (100 ml). The oil obtained was extracted into ethyl acetate, filtered to remove some insoluble material (0.4 g), dried and evaporated to dryness. The residue was crystallised from ethanol to give three crops of 2-(acetylmethylthio)benzimidazole (2), as colourless crystals, 15.0 g, 73%, mp. 112°-113° C. PMR was consistent with a tautomeric mixture of the open chain and ring closed forms.

Workup

  1. temperaturerefluxed for 5 hrs
  2. custom21.24 g, 88% was isolated by filtration
  3. washwashed with acetone and air
  4. customdried
  5. dissolutionThe salt was dissolved in water (150 ml)
  6. customThe oil obtained
  7. extractionwas extracted into ethyl acetate
  8. filtrationfiltered
  9. customto remove some insoluble material (0.4 g)
  10. customdried
  11. customevaporated to dryness
  12. customThe residue was crystallised from ethanol

Sources & evidence

ORD record
ord-725e6ce79a744f529d5ebc57c18d780c
Source dataset
uspto-grants-1993_05
Patent number
US05210209

Reaction notes

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