Methylamine → Benzoic acid, 2-chloro-5-[(methylamino)sulfonyl]-

HRID 32670Notes

Reaction equation

HRID 32670 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([S:11]([OH:13])=[O:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH3:14][NH2:15]>O1CCOCC1>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([S:11](=[O:13])(=[O:12])[NH:15][CH3:14])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 151129042-Chloro-5-sulfino-benzoic acid

Product 1

HCID 111724Benzoic acid, 2-chloro-5-[(methylamino)sulfonyl]-Yield 72.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 1 g (4 mmol) 2-Chloro-5-sulfino-benzoic acid and 0.62 g (20 mmol) Methylamine in 10 ml dioxane was stirred for 3 h at room temperature. After evaporation of the volatiles 15 ml 5N HCl was added and the mixture was extracted 3× with ethylacetate. The solvent was removed under vacuum to yield 0.724 g (72%) of the title compound as amorphous white solid. MS (m/e): 248.1 (MH−, 100%).

Workup

  1. customAfter evaporation of the volatiles 15 ml 5N HCl
  2. additionwas added
  3. extractionthe mixture was extracted 3× with ethylacetate
  4. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-99e1bb6a5152417c91d818557afbaf55
Source dataset
uspto-grants-2008_09
Patent number
US07427612B2

Reaction notes

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