Methanol → Methyl 4-sulphamoylbenzoate

HRID 655614Notes

Reaction equation

HRID 655614 reaction equation
[NH2:1][S:2]([C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][CH:6]=1)(=[O:4])=[O:3].S(Cl)(Cl)=O.[CH3:18]O>>[NH2:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([C:9]([O:11][CH3:18])=[O:10])=[CH:12][CH:13]=1)(=[O:3])=[O:4]

Participants

4

Reactant 3

HCID 887MethanolHCID 8739CarzenideHCID 24386Thionyl Chloride

Product 1

HCID 89847Methyl 4-sulphamoylbenzoateYield 75%

Procedure

To a suspension of 4-(aminosulfonyl)benzoic acid (500 mg, 2.5 mmol) in MeOH (2 ml) at 0° C. is added thionylchloride (0.2 ml, 7.4 mmol). The reaction mixture is stirred at rt overnight. When TLC confirms the total consumption of the starting acid, the solvent and excess thionyl chloride are removed under reduced pressure to afford 400 mg (75%) of the title compound, which was used in the next step without any further purification. LC/MS: (ES+):215.9, (ES−):214.1.

Workup

  1. customthe total consumption of the starting acid
  2. customthe solvent and excess thionyl chloride are removed under reduced pressure

Sources & evidence

ORD record
ord-e6c34b6f574d4834a2b979ebaca7a874
Source dataset
uspto-grants-2011_12
Patent number
US08071597B2

Reaction notes

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