Diazomethane → 5-Tert-butylsulfamoyl-4-chloro-2-ethoxybenzoic acid methyl ester

HRID 2263926Notes

Reaction equation

HRID 2263926 reaction equation
[C:1]([NH:5][S:6]([C:9]1[C:10]([Cl:21])=[CH:11][C:12]([O:18][CH2:19][CH3:20])=[C:13]([CH:17]=1)[C:14]([OH:16])=[O:15])(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2].[N+](=[CH2:24])=[N-]>O1CCCC1>[CH3:24][O:15][C:14](=[O:16])[C:13]1[CH:17]=[C:9]([S:6](=[O:8])(=[O:7])[NH:5][C:1]([CH3:4])([CH3:3])[CH3:2])[C:10]([Cl:21])=[CH:11][C:12]=1[O:18][CH2:19][CH3:20]

Participants

4

Reactant 2

HCID 9550DiazomethaneHCID 670713515-tert-Butylsulfamoyl-4-chloro-2-ethoxybenzoic acid

Product 1

HCID 588942525-Tert-butylsulfamoyl-4-chloro-2-ethoxybenzoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-tert-Butylsulfamoyl-4-chloro-2-ethoxybenzoic acid (0.8 g, 24 mmol) in 10 mL of tetrahydrofuran was treated with diazomethane (15 mL, ˜2-3 M in ether, prepared from N-methyl-N-nitroso-p-toluenesulfonamide, Aldrich) at room temperature and stirred for 0.5 h. The mixture was concentrated, and the residue was purified by flash chromatography (silica gel, eluting with 20% ethyl acetate in hexane) to give 0.45 g of 5-tert-butylsulfamoyl-4-chloro-2-ethoxybenzoic acid methyl ester as a solid.

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue was purified by flash chromatography (silica gel, eluting with 20% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-94456d28879e4a57b2bc50007576605a
Source dataset
uspto-grants-2010_12
Patent number
US07851626B2

Reaction notes

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