Water → Methyl 3-(methylsulfonamido)-5-nitrobenzoate

HRID 1957959Notes

Reaction equation

HRID 1957959 reaction equation
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[C:6]([NH2:13])[CH:5]=1.N1C=CC=CC=1.[CH3:21][S:22](Cl)(=[O:24])=[O:23].O>ClCCl>[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[C:6]([NH:13][S:22]([CH3:21])(=[O:24])=[O:23])[CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 2756518Methyl 3-amino-5-nitrobenzoate

Product 1

HCID 57815097Methyl 3-(methylsulfonamido)-5-nitrobenzoateYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-amino-5-nitro-benzoic acid methyl ester (25 g; 0.13 mol) was dissolved in to dichloromethane (300 ml) and treated at 0° C. with 11 ml of pyridine. Methanesulfonylchloride (11 ml; 0.14 mol) was added and the reaction mixture was stirred overnight at room temperature. Water was added and the precipitate filtered and washed with dichloromethane/diethylether. 32 g (0.11 mmol; 89% yield) of 3-methylsulfonylamino-5-nitro-benzoic acid methyl ester were obtained as a solid.

Workup

  1. filtrationthe precipitate filtered
  2. washwashed with dichloromethane/diethylether

Sources & evidence

ORD record
ord-ef63bf4475214897a7df71938f397b48
Source dataset
uspto-grants-2013_04
Patent number
US08410100B2

Reaction notes

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