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

HRID 547520

反応式

HRID 547520 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

HCID 33533142-acetamido-N-(4-nitrophenyl)benzamide収率 55%

試薬・触媒・溶媒 1

HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
57.5 °C

実験手順

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%.

後処理

  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

出典と根拠

ORDレコード
ord-98575b1f5f1c4b22bb9bf237dcaca054
出典データセット
uspto-grants-2011_05
特許番号
US07939546B2

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