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Methanol → Methyl 4-chloro-3-sulfamoylbenzoate

HRID 734733
Notes
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Reaction equation

HRID 734733 reaction equation
[NH2:1][S:2]([C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][C:13]=1[Cl:14])[C:8]([OH:10])=[O:9])(=[O:4])=[O:3].[CH3:15]O>S(=O)(=O)(O)O.CCOC(C)=O>[NH2:1][S:2]([C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][C:13]=1[Cl:14])[C:8]([O:10][CH3:15])=[O:9])(=[O:4])=[O:3]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 887MethanolHCID 145684-Chloro-3-sulfamoylbenzoic acid

Product 1

HCID 4277179Methyl 4-chloro-3-sulfamoylbenzoateYield 95%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 8857Ethyl AcetateSolvent

Procedure

3-(Aminosulfonyl)-4-chlorobenzoic acid (943 mg, 4.0 mmol) was heated at 70° C. in CH3OH (10 mL) with 3 drops of concentrated sulfuric acid for 34 hours. The reaction mixture was diluted with EtOAc (20 mL), washed with water, brine, and dried (Na2SO4). The solvent was evaporated to afford the product (950 mg, 95%) as a white solid. MS (ES+) m/z 250 [M+H]+.

Workup

  1. washwashed with water, brine
  2. dry with materialdried (Na2SO4)
  3. customThe solvent was evaporated

Sources & evidence

ORD record
ord-2ba078ff6fe9468996bc53adcbb229cd
Source dataset
uspto-grants-2009_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07592357B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes