Benzenesulfonamide → N-benzenesulfonyl-4-acetylamino-3-nitrobenzamide

HRID 276023

반응식

HRID 276023 반응식
[C:1]([NH:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=O)=[CH:7][C:6]=1[N+:14]([O-:16])=[O:15])(=[O:3])[CH3:2].[C:17]1([S:23]([NH2:26])(=[O:25])=[O:24])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C1(C2CCCCCCCCCC=2)CCCCCCCCNN=1>CN(C)C=O>[C:17]1([S:23]([NH:26][C:9](=[O:11])[C:8]2[CH:12]=[CH:13][C:5]([NH:4][C:1](=[O:3])[CH3:2])=[C:6]([N+:14]([O-:16])=[O:15])[CH:7]=2)(=[O:25])=[O:24])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

참가 물질

5

반응물 3

HCID 7370BenzenesulfonamideHCID 737584-Acetamido-3-nitrobenzoic acidHCID 536302743-(Cycloundecen-1-yl)-1,2-diazacycloundec-2-ene

생성물 1

HCID 18315416N-benzenesulfonyl-4-acetylamino-3-nitrobenzamide수율 78.2%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

N,N′-carbonyldiimidazole (14.45 g) was added to a solution of 10.00 g of 4-acetylamino-3-nitrobenzoic acid in 300 ml of N,N-dimethylformamide, and the mixture was stirred at room temperature for 1 hour. Subsequently, 14.03 g of benzenesulfonamide and 13.58 g of diazabicycloundecene were added thereto, and the mixture was stirred at 100° C. for 72 hours. The reaction mixture was separated with the addition of chloroform and water. The organic layer was then concentrated, and the resulting residue was purified through silica-gel column chromatography (eluent: a mixture of ethyl acetate and methanol at a ratio of 4:1) to give 12.67 g of N-benzenesulfonyl-4-acetylamino-3-nitrobenzamide.

후처리

  1. stirringthe mixture was stirred at 100° C. for 72 hours
  2. customThe reaction mixture was separated with the addition of chloroform and water
  3. concentrationThe organic layer was then concentrated
  4. customthe resulting residue was purified through silica-gel column chromatography (eluent
  5. additiona mixture of ethyl acetate and methanol at a ratio of 4:1)

출처 및 근거

ORD 기록
ord-5431c869c2e0400b9d0d9f80ddb4dede
출처 데이터셋
uspto-grants-2002_03
특허 번호
US06352985B1

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