Aniline → O-Ethylacetanilide

HRID 925026

반응식

HRID 925026 반응식
[CH2:1]([C:3]1[CH:9]=[CH:8][CH:7]=[CH:6][C:4]=1[NH2:5])[CH3:2].CCN(CC)CC.[C:17](Cl)(=[O:19])[CH3:18].NC1C=CC=CC=1>O.ClCCl>[CH2:1]([C:3]1[CH:9]=[CH:8][CH:7]=[CH:6][C:4]=1[NH:5][C:17](=[O:19])[CH3:18])[CH3:2]

참가 물질

7

반응물 4

HCID 6115AnilineHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 113572-Ethylaniline

생성물 1

HCID 36332O-Ethylacetanilide수율 58%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

2-ethylaniline (12.4 mL, 100 mmol) and NEt3 (15.4 mL, 110 mmol) were added to 100 mL of dichloromethane and cooled to 0° C. Acetyl chloride (7.10 mL 100 mmol) was added dropwise to the cooled aniline solution, affording a peach colored suspension after complete addition. The slurry was warmed to room temperature and heated to reflux overnight. The suspension was taken to dryness and the solid was treated with 200 mL of water. The solid was collected by filtration, washed with 200 mL of diethylether and dried in vacuo, yielding 9.45 g (58%) of white solid. 1H NMR (400 MHz, CDCl3): 7.68 (d, 1H), 7.26-7.11 (m, 4H), 2.59 (q, 2H), 2.18 (s, 3H), 1.22 (t, 3H).

후처리

  1. customaffording a peach colored suspension
  2. additionafter complete addition
  3. temperatureThe slurry was warmed to room temperature
  4. temperatureheated
  5. temperatureto reflux overnight
  6. filtrationThe solid was collected by filtration
  7. washwashed with 200 mL of diethylether
  8. customdried in vacuo

출처 및 근거

ORD 기록
ord-aee044eca39b4b1f8590e87e55ace7c8
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09283555B2

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