4-Chloroaniline → Benzamide, 5-chloro-N-(4-chlorophenyl)-2-nitro-

HRID 844140

反応式

HRID 844140 の反応式
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N+:11]([O-:13])=[O:12])=[C:6]([CH:10]=1)[C:7](Cl)=[O:8].C(N(CC)CC)C.[Cl:21][C:22]1[CH:28]=[CH:27][C:25]([NH2:26])=[CH:24][CH:23]=1>C(Cl)Cl>[Cl:21][C:22]1[CH:28]=[CH:27][C:25]([NH:26][C:7](=[O:8])[C:6]2[CH:10]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=2[N+:11]([O-:13])=[O:12])=[CH:24][CH:23]=1

参加物

5

反応物 3

HCID 78124-ChloroanilineHCID 8471TriethylamineHCID 27236855-Chloro-2-nitrobenzoyl chloride

生成物 1

HCID 873788Benzamide, 5-chloro-N-(4-chlorophenyl)-2-nitro-収率 96.4%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

To a solution of 5-chloro-2-nitrobenzoyl chloride (23 g, 100 mmol) in methylene chloride (200 mL) at 0° C. was added triethylamine (16 mL, 115 mmol), followed by 4-chloroaniline (14 g, 110 mmol). The mixture was stirred for 20 minutes at 0° C., then warmed to ambient temperature. After 5 hours, the mixture was concentrated of all volatiles in vacuo. The residual solid was dissolved in ethyl acetate (400 mL) and washed with water (200 mL), 1M hydrochloric acid (2×200 mL), 1M sodium bicarbonate (200 mL) and brine (200 mL) and dried over MgSO4. Concentration and drying in vacuo afforded 30 g (93% yield) of N-(4-chlorophenyl)-5-chloro-2-nitrobenzamide; NMR (CDCl3) 8.1 (d, 1), 7.7 (br, 1), 7.6 (m, 2), 7.5 (d, 2), 7.3 (d, 2) ppm.

後処理

  1. temperaturewarmed to ambient temperature
  2. waitAfter 5 hours
  3. concentrationthe mixture was concentrated of all volatiles in vacuo
  4. dissolutionThe residual solid was dissolved in ethyl acetate (400 mL)
  5. washwashed with water (200 mL), 1M hydrochloric acid (2×200 mL), 1M sodium bicarbonate (200 mL) and brine (200 mL)
  6. dry with materialdried over MgSO4
  7. concentrationConcentration
  8. customdrying in vacuo

出典と根拠

ORDレコード
ord-0071735323cf4cddaff909fd768abfec
出典データセット
uspto-grants-2002_04
特許番号
US06380221B1

関連ノート

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