Ammonia → Methyl 4-(methanesulfonamidomethyl)-2-sulfamoylbenzoate

HRID 1816540Notes

Reaction equation

HRID 1816540 reaction equation
Cl[S:2]([C:5]1[CH:14]=[C:13]([CH2:15][NH:16][S:17]([CH3:20])(=[O:19])=[O:18])[CH:12]=[CH:11][C:6]=1[C:7]([O:9][CH3:10])=[O:8])(=[O:4])=[O:3].[NH3:21]>C1COCC1>[S:2]([C:5]1[CH:14]=[C:13]([CH2:15][NH:16][S:17]([CH3:20])(=[O:19])=[O:18])[CH:12]=[CH:11][C:6]=1[C:7]([O:9][CH3:10])=[O:8])(=[O:4])(=[O:3])[NH2:21]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 22494947Methyl 2-(chlorosulfonyl)-4-[[(methylsulfonyl)amino]methyl]benzoate

Product 1

HCID 17937780Methyl 4-(methanesulfonamidomethyl)-2-sulfamoylbenzoateYield 80.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 11 g (32 mmol) of methyl 2-chlorosulfonyl-4-methanesulfonylaminomethylbenzoate in 200 ml of THF is treated at 0° C. with 1.1 g (64 mmol) of NH3 gas. For work-up, the mixture is concentrated in vacuo. Extracting the residue by stirring with water and then filtration and drying in vacuo give 8.3 g (80%) of methyl 2-sulfamoyl4-methanesulfonylaminomethylbenzoate of melting point 185-187° C.

Workup

  1. concentrationFor work-up, the mixture is concentrated in vacuo
  2. extractionExtracting the residue
  3. filtrationfiltration
  4. customdrying in vacuo

Sources & evidence

ORD record
ord-412b20fc7a5949b6955ef2d00ecaa5b2
Source dataset
uspto-grants-2005_04
Patent number
US06884903B2

Reaction notes

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