Hydrochloric Acid → Methyl 4-sulphamoylbenzoate

HRID 981064Notes

Reaction equation

HRID 981064 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH2:13])(=[O:12])=[O:11])=[CH:6][CH:5]=1)([OH:3])=[O:2].Cl.[CH3:15]O>>[CH3:15][O:2][C:1](=[O:3])[C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH2:13])(=[O:12])=[O:11])=[CH:6][CH:5]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 8739Carzenide

Product 1

HCID 89847Methyl 4-sulphamoylbenzoate

Procedure

A slurry of 30.2 g (0.15 mole) of p-carboxybenzenesulfonamide in 500 ml of methanol was treated with 30 g of anhydrous hydrogen chloride and the mixture was heated at reflux temperature for 3 hr. The solution was concentrated under vacuum to give 32.3 g of white, crystalline residue. A 5.0 g portion of this residue was recrystallized from 25 ml of methanol to give 3.3 g of title compound as a white powder, mp 174°-178° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux temperature for 3 hr
  3. concentrationThe solution was concentrated under vacuum
  4. customto give 32.3 g of white, crystalline residue
  5. customA 5.0 g portion of this residue was recrystallized from 25 ml of methanol

Sources & evidence

ORD record
ord-d7cf1793c45c47e48b0a12df4fda5151
Source dataset
uspto-grants-1991_02
Patent number
US04990523

Reaction notes

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