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

HRID 321972
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HRID 321972 반응식
C([NH:4][C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][C:13]=1[N+:14]([O-:16])=[O:15])[C:8]([OH:10])=O)(=O)C.[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:8](=[O:10])[C:7]2[CH:11]=[CH:12][C:13]([N+:14]([O-:16])=[O:15])=[C:5]([NH2:4])[CH:6]=2)(=[O:25])=[O:24])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 7370BenzenesulfonamideHCID 39330783-Acetamido-4-nitrobenzoic acidHCID 536302743-(Cycloundecen-1-yl)-1,2-diazacycloundec-2-ene

생성물 1

HCID 18315560N-benzenesulfonyl-3-amino-4-nitrobenzamide수율 50.2%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

N,N′-carbonyldiimidazole (28.9 g) is added to an N,N-dimethylformamide (300 ml) solution of 3-acetylamino-4-nitro-benzoic acid (20.0 g), and the solution is stirred for 1 hour at room temperature. Further, benzenesulfonamide (28.0 g) and diazabicycloundecene (27.16 g) are added to the solution and the solution is stirred for 4 days at 100° C. The solvent is removed through evaporation under reduced pressure. Chloroform and 10% sodium hydroxide aqueous solution are added to the residue, and the mixture is stirred briskly. 10% hydrochloric acid is added to the aqueous layer until neutral. Chloroform is added and the solution is stirred briskly. The precipitated crystals are separated through filtration, and are dried. Thus, N-benzenesulfonyl-3-amino-4-nitrobenzamide (14.4 g) is obtained.

후처리

  1. stirringthe solution is stirred for 4 days at 100° C
  2. customThe solvent is removed through evaporation under reduced pressure
  3. additionChloroform and 10% sodium hydroxide aqueous solution are added to the residue
  4. stirringthe mixture is stirred briskly
  5. addition10% hydrochloric acid is added to the aqueous layer until neutral
  6. additionChloroform is added
  7. stirringthe solution is stirred briskly
  8. customThe precipitated crystals are separated through filtration
  9. customare dried

출처 및 근거

ORD 기록
ord-6718aa49e1c54bb0b543d12d6dbefcd3
출처 데이터셋
uspto-grants-2001_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06211177B1

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