Dimethylformamide → N-(1-butanesulfonyl)-4-acetylamino-3-nitrobenzamide

HRID 1699640

Reaction equation

HRID 1699640 reaction equation
CN(C)C=O.[C:6]([NH:9][C:10]1[CH:18]=[CH:17][C:13]([C:14]([OH:16])=O)=[CH:12][C:11]=1[N+:19]([O-:21])=[O:20])(=[O:8])[CH3:7].[CH2:22]([S:26]([NH2:29])(=[O:28])=[O:27])[CH2:23][CH2:24][CH3:25].C1(C2CCCCCCCCCC=2)CCCCCCCCNN=1>O.C(Cl)(Cl)Cl>[CH2:22]([S:26]([NH:29][C:14](=[O:16])[C:13]1[CH:17]=[CH:18][C:10]([NH:9][C:6](=[O:8])[CH3:7])=[C:11]([N+:19]([O-:21])=[O:20])[CH:12]=1)(=[O:28])=[O:27])[CH2:23][CH2:24][CH3:25]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 184601-ButanesulfonamideHCID 737584-Acetamido-3-nitrobenzoic acidHCID 536302743-(Cycloundecen-1-yl)-1,2-diazacycloundec-2-ene

Product 1

HCID 18680978N-(1-butanesulfonyl)-4-acetylamino-3-nitrobenzamideYield 70.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

N,N′-carbonyldiimidazole (9.40 g) is added to an N,N-dimethylformamide (300 ml) solution of 4-acetylamino-3-nitro-benzoic acid (10.0 g), and the solution is stirred for 1 hour at room temperature. Then, 1-butanesulfonamide (7.92 g) and diazabicycloundecene (8.83 g) are added into the solution, and the solution is stirred for 72 hours at 100° C. After chloroform and water are added into the solution and the solution is separated into layers, the residue, which is obtained by concentrating the organic layer, is purified using silica gel column chromatography (eluate: ethyl acetate/methanol=4/1), and thus, N-(1-butanesulfonyl)-4-acetylamino-3-nitrobenzamide (10.75 g) is obtained. 1H-NMR (DMSO-d6, δ): 0.87 (3H, t, J=7.4 Hz), 1.37-1.44 (2H, m), 1.64-1.71 (2H, m), 2.12 (3H, s), 3.52 (2H, t, J=7.7 Hz), 7.83 (1H, d, J=8.6 Hz), 8.21 (1H, dd, J=8.6 and 2.1 Hz), 8.54 (1H, d, J=2.2 Hz), 10.56 (1H, s), 12.32 (1H, s).

Workup

  1. stirringthe solution is stirred for 72 hours at 100° C
  2. customthe solution is separated into layers
  3. customthe residue, which is obtained
  4. concentrationby concentrating the organic layer
  5. customis purified

Sources & evidence

ORD record
ord-c6b5408aa689489d99c4c281a89c5861
Source dataset
uspto-grants-2002_02
Patent number
US06348032B1

Linked notes

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