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

HRID 1711339

반응식

HRID 1711339 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

반응 조건

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, 1H, NH), 10.15 (s, 1 H, NH), 8.29 (m, 2H, H-3′ & H-5′), 8.12 (t, J=1.8 Hz, 1H, H-2), 7.84 (br dd, J=8.1, 1.2 Hz, 1H, H-6), 7.65 (td, J=7.8, 2.5 Hz, 1H, 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-037d80ef2bd5454e8a3eee08e52a1db4
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07790746B2

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