Chloroform → Methyl 4-sulphamoylbenzoate

HRID 351119Notes

Reaction equation

HRID 351119 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH2:13])(=[O:12])=[O:11])=[CH:6][CH:5]=1)([OH:3])=[O:2].[CH:14](Cl)(Cl)Cl.C[Si](C=[N+]=[N-])(C)C>CO>[CH3:14][O:2][C:1](=[O:3])[C:4]1[CH:9]=[CH:8][C:7]([S:10](=[O:12])(=[O:11])[NH2:13])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 6212ChloroformHCID 8739CarzenideHCID 167693Trimethylsilyldiazomethane

Product 1

HCID 89847Methyl 4-sulphamoylbenzoateYield 98%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-Carboxyphenylsulfonamide (2.00 g, 9.9 mmol) is suspended in 3:1 chloroform:methanol (200 mL). (Trimethylsilyl)-diazomethane is added as a 2.0 M solution in Hexanes (7.4 mL, 14.8 mmol) at ambient temperature and stirred for 5 min. The solution is concentrated in vacuo, and the crude is chromatographed on silica gel, 0.5% MeOH/0.1% AcOH in CH2Cl2. The product is a white solid, 2.11 g, 98% yield.

Workup

  1. concentrationThe solution is concentrated in vacuo
  2. customthe crude is chromatographed on silica gel, 0.5% MeOH/0.1% AcOH in CH2Cl2

Sources & evidence

ORD record
ord-438058aeb17b4f459ea6c9c8760faca3
Source dataset
uspto-grants-2007_02
Patent number
US07183320B2

Reaction notes

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