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3,4-Dimethylaniline → 4-amino-N-(3,4-dimethylphenyl)-3-nitrobenzamide

HRID 1514979
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HRID 1514979 반응식
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.[CH3:35][C:36]1[CH:37]=[C:38]([NH2:43])[CH:39]=[CH:40][C:41]=1[CH3:42].CCN(C(C)C)C(C)C>CN(C=O)C.CCOC(C)=O.O>[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:43][C:38]2[CH:39]=[CH:40][C:41]([CH3:42])=[C:36]([CH3:35])[CH:37]=2)=[O:8])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12]
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참가 물질

9

반응물 5

HCID 72483,4-DimethylanilineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 74115Benzoic acid, 4-amino-3-nitro-HCID 757711-HydroxybenzotriazoleHCID 81531Diisopropylethylamine

생성물 1

HCID 87439264-amino-N-(3,4-dimethylphenyl)-3-nitrobenzamide

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 4-amino-3-nitrobenzoic acid (1.82 g) in DMF (20 mL) was added HOBT (1.49 g) and EDCI (2.1 g). After stirring at room temperature for 10 min, 3,4-dimethylphenylamine (1.2 g) and DIPEA (5.3 mL) were added. The solution was stirred at room temperature for 18 h then the mixture was partioned between water and EtOAc The aqueous layer was extracted with EtOAc. The combined organic layers were washed with water, brine, dried, filtered and concentrated. The residue was purified by recrystallization from EtOAc and gave 4-amino-N-(3,4-dimethylphenyl)-3-nitrobenzamide as a yellow solid. MS (ESI)m/z 286 (M+H).

후처리

  1. stirringThe solution was stirred at room temperature for 18 h
  2. extractionwas extracted with EtOAc
  3. washThe combined organic layers were washed with water, brine
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by recrystallization from EtOAc

출처 및 근거

ORD 기록
ord-29bcb15f6d4745fda8e136e230a249b0
출처 데이터셋
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08222248B2

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