Water → 2-acetamido-N-(4-nitrophenyl)benzamide

HRID 547520

반응식

HRID 547520 반응식
[C:1]([NH:4][C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=1)C(O)=O)(=[O:3])[CH3:2].C1N=CN([C:19]([N:21]2C=N[CH:23]=[CH:22]2)=[O:20])C=1.[N+:26]([C:29]1[CH:35]=CC(N)=[CH:31][CH:30]=1)([O-:28])=[O:27].O>CN1CCCC1=O>[C:1]([NH:4][C:5]1[CH:13]=[CH:12][CH:11]=[CH:7][C:6]=1[C:19]([NH:21][C:22]1[CH:23]=[CH:35][C:29]([N+:26]([O-:28])=[O:27])=[CH:30][CH:31]=1)=[O:20])(=[O:3])[CH3:2]

참가 물질

6

반응물 4

HCID 962WaterHCID 74754-NitroanilineHCID 488473-Acetamidobenzoic acidHCID 682631,1'-Carbonyldiimidazole

생성물 1

HCID 33533142-acetamido-N-(4-nitrophenyl)benzamide수율 55%

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매

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온도
57.5 °C

실험 절차

A mixture of 3-acetamidobenzoic acid (C1) (5.30 g, 29.58 mmol) and CDI (5.75 g, 35.50 mmol, 1.2 equivalent) in N-methylpyrrolidinone (20 mL) was heated at 55-60° C. for 2 h. 4-Nitroaniline (6.13 g, 44.37 mmol, 1.5 equivalent) was then added and the mixture was heated to 140° C. for 4 h, then poured into water (400 mL) and stirred for 18 h. The resulting precipitate was filtered and washed sequentially with water and CH2Cl2 and then crystallized from MeOH to give C2 (4.84 g; 55%) as a yellow solid; mp (MeOH) 259-261° C.; 1H NMR [(CD3)2SO] δ 10.80 (s, 1 H, NH), 10.15 (s, 1 H, NH), 8.29 (m, 2 H, H-{acute over (3)}& H-{acute over (5)}), 8.12 (t, J=1.8 Hz, 1 H, H-2), 7.84 (br dd, J=8.1, 1.2 Hz, 1 H, H-6), 7.65 (td, J=7.8, 2.5 Hz, 1 H, H-4), 7.48 (t, J=7.9 Hz, 1 H, H-5), 2.08 (s, 3H, COCH3); Anal. Calc. For C15H13N3O4: C, 60.2; H, 4.4; N, 14.0; found C, 60.4; H, 4.6; N, 14.1%.

후처리

  1. temperaturethe mixture was heated to 140° C. for 4 h
  2. filtrationThe resulting precipitate was filtered
  3. washwashed sequentially with water and CH2Cl2
  4. customcrystallized from MeOH

출처 및 근거

ORD 기록
ord-98575b1f5f1c4b22bb9bf237dcaca054
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07939546B2

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