Carzenide → Methyl 4-sulphamoylbenzoate

HRID 2376209Notes

Reaction equation

HRID 2376209 reaction equation
[S:1]([C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][CH:6]=1)(=[O:4])(=[O:3])[NH2:2].[CH2:14](Cl)Cl.CO.[Si](C=[N+]=[N-])(C)(C)C>CCCCCC.[OH-].[Na+].C(Cl)Cl>[CH3:14][O:10][C:9](=[O:11])[C:8]1[CH:7]=[CH:6][C:5]([S:1](=[O:3])(=[O:4])[NH2:2])=[CH:13][CH:12]=1

Participants

7

Reactant 3

HCID 8739CarzenideHCID 167693TrimethylsilyldiazomethaneHCID 21226129Dichloromethane methanol

Product 1

HCID 89847Methyl 4-sulphamoylbenzoateYield 95%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8058HexaneSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a stirred suspension of 4-sulfamoyl-benzoic acid (25.0 g, 0.124 mol) in 4:1 CH2Cl2/MeOH at rt was added 1.0 M TMSCHN2 in hexane (175 mL), and the reaction mixture was allowed to stir for 2 h. The mixture was diluted with 1N NaOH (100 mL) and CH2Cl2 (150 mL), and the layers were separated. The organic layer was dried over Na2SO4, then filtered, and the solvent was removed under reduced pressure to afford the desired ester (25.2 g, 95%), which was used without further purification. 1H NMR (400 MHz, DMSO-d6): 8.14 (d, J=8.1 Hz, 2H), 7.96 (d, J=8.1 Hz, 2H), 7.58 (s, 2H), 3.90 (s, 3H).

Workup

  1. customthe layers were separated
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-812c2fcde3144d1aa899994b05369843
Source dataset
uspto-grants-2008_12
Patent number
US07465808B2

Reaction notes

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