Water → 4,4'-Dichloro-2'-methylbenzanilide

HRID 1016646

반응식

HRID 1016646 반응식
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.[Cl:11][C:12]1[CH:18]=[CH:17][C:15]([NH2:16])=[C:14]([CH3:19])[CH:13]=1.C(N(CC)CC)C.O>ClCCl>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:16][C:15]2[CH:17]=[CH:18][C:12]([Cl:11])=[CH:13][C:14]=2[CH3:19])=[O:7])=[CH:4][CH:3]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 72514-Chloro-2-toluidineHCID 8471TriethylamineHCID 85014-Chlorobenzoyl chloride

생성물 1

HCID 2952414,4'-Dichloro-2'-methylbenzanilide수율 92%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

4-Chlorobenzoyl chloride (19.5 g, 111 mmol) was added over 10 min. to a stirred, cooled (0° C.) solution of 4-chloro-2-methylaniline (15 g, 106 mmol) and triethylamine (22.2 mL, 16.1 g, 159 mmol) in dichloromethane (300 mL) and the mixture was stirred at room temperature for 2 h. Water (100 mL) was added and the dichloromethane was evaporated under reduced pressure. Aqueous sodium hydrogen carbonate (saturated, 200 mL), water (200 mL) and ethyl acetate (1000 mL) were added and the layers were separated. The organic layer was dried (MgSO4) and the solvent was evaporated under reduced pressure. The residue was triturated with ether and the solid was collected and dried in vacuo to give the title compound (27.3 g, 92%). 1H NMR (360 MHz, CDCl3) δ 7.82 (3H, m), 7.79 (1H, br s), 7.48 (2H, d, J 8.5 Hz), 7.23 (2H, m), and 2.30 (3H, s).

후처리

  1. customthe dichloromethane was evaporated under reduced pressure
  2. additionAqueous sodium hydrogen carbonate (saturated, 200 mL), water (200 mL) and ethyl acetate (1000 mL) were added
  3. customthe layers were separated
  4. dry with materialThe organic layer was dried (MgSO4)
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was triturated with ether
  7. customthe solid was collected
  8. customdried in vacuo

출처 및 근거

ORD 기록
ord-175a1f612a8a4c78aac9bb2b4b160f6e
출처 데이터셋
uspto-grants-2002_11
특허 번호
US06476045B2

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