Triethylamine → 4-(dibenzylsulfamoyl)benzoic acid

HRID 1058986Notes

Reaction equation

HRID 1058986 reaction equation
Cl.CN[O:4]C.C(N(CC)CC)C.[CH2:13]([N:20]([CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[S:21]([C:24]1[CH:32]=[CH:31][C:27]([C:28](Cl)=[O:29])=[CH:26][CH:25]=1)(=[O:23])=[O:22])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(Cl)Cl>[CH2:13]([N:20]([CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[S:21]([C:24]1[CH:32]=[CH:31][C:27]([C:28]([OH:4])=[O:29])=[CH:26][CH:25]=1)(=[O:23])=[O:22])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 18669513HCID 18669513, compound

Product 1

HCID 45523624-(dibenzylsulfamoyl)benzoic acidYield 92.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of N,O-dimethylhydroxylamine hydrochloride (7.37 g; 75.6 mmoles) and triethylamine (21.8 ml; 151 mmoles) in methylene chloride (150 ml), another solution of 4-(dibenzylsulfamoyl)benzoyl chloride (25 g) in methylene chloride (150 ml) was slowly added and the resulting mixture stirred at room temperature for 16 hours. The solid was filtered off, the solvent removed under reduced pressure and the residual oil purified by column chromatography with silica gel and n-hexane-ethyl acetate 1:1 as eluent. N,O-dimethylamide of 4-(dibenzylsulfamoyl)benzoic acid (22 g) was obtained, m.p. 75° C.

Workup

  1. filtrationThe solid was filtered off
  2. customthe solvent removed under reduced pressure
  3. customthe residual oil purified by column chromatography with silica gel and n-hexane-ethyl acetate 1:1 as eluent

Sources & evidence

ORD record
ord-ddafc815cb8d4d18ad11b2cd9cd0a599
Source dataset
uspto-grants-2003_02
Patent number
US06518303B2

Reaction notes

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