Water → 4-nitro-N-(4-sulfamoylbenzyl)-benzamide

HRID 497306

Reaction equation

HRID 497306 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8](Cl)=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].Cl.[NH2:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([S:22]([NH2:25])(=[O:24])=[O:23])=[CH:18][CH:17]=1.C(N(CC)CC)C.O>C(#N)C>[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([NH:14][CH2:15][C:16]2[CH:17]=[CH:18][C:19]([S:22](=[O:24])(=[O:23])[NH2:25])=[CH:20][CH:21]=2)=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 85024-Nitrobenzoyl chlorideHCID 67313Mafenide Hydrochloride

Product 1

HCID 41284264-nitro-N-(4-sulfamoylbenzyl)-benzamideYield 85.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A solution of 4-nitrobenzoylchloride (1.85 g, 1 eq.) in acetonitrile (20 ml) was added to a solution of 4-aminomethyl-benzenesulfonamide hydrochloride (4.44 g, 2 eq.) and triethylamine (2.78 ml, 2 eq.) in acetonitrile (40 ml) at 0° C. under inert atmosphere. After the addition was completed, the mixture was warmed to rt and stirred for 3 d. Water was added and the mixture was concentrated under reduced pressure. The resulting precipitate was filtered off and washed with water and methanol to yield 2.86 g (85%) of 4-nitro-N-(4-sulfamoylbenzyl)-benzamide.

Workup

  1. additionAfter the addition
  2. concentrationthe mixture was concentrated under reduced pressure
  3. filtrationThe resulting precipitate was filtered off
  4. washwashed with water and methanol

Sources & evidence

ORD record
ord-f9cc2f8284194a4faf905b221ca29666
Source dataset
uspto-grants-2005_09
Patent number
US06949567B2

Linked notes

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