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

HRID 2300900

반응식

HRID 2300900 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-592cee0fce8a4b788aab33340f97aa5f
출처 데이터셋
uspto-grants-2002_12
특허 번호
US06498185B1

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