Water → 3-(1-Chloroethyl)benzamide

HRID 550753노트

반응식

HRID 550753 반응식
CCN(C1C=CC=CC=1)CC.O[CH:13]([C:15]1[CH:16]=[C:17]([CH:21]=[CH:22][CH:23]=1)[C:18]([NH2:20])=[O:19])[CH3:14].S(Cl)([Cl:26])=O.O>C(Cl)Cl>[Cl:26][CH:13]([C:15]1[CH:16]=[C:17]([CH:21]=[CH:22][CH:23]=1)[C:18]([NH2:20])=[O:19])[CH3:14]

참가 물질

6

반응물 4

HCID 962WaterHCID 7061N,N-DiethylanilineHCID 24386Thionyl ChlorideHCID 2812153-(1-Hydroxyethyl)benzamide

생성물 1

HCID 666233683-(1-Chloroethyl)benzamide수율 75%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Diethylaniline (390 μL, 2.45 mmol) was added 3-(1-hydroxyethyl)benzamide (400 mg, 2.45 mmol) slurried in DCM (20 mL) and the reaction mixture was cooled with an ice -bath. Thionyl chloride ((255 μL, 2.47 mmol) was added dropwise and the reaction was put in the refrigerator overnight. Water was added, the reaction mixture was extracted twice with DCM, washed with a 10% HCl solution, neutralized with a saturated bicarbonate solution, treated with brine, dried (MgSO4), filtered and evaporated to dryness. The crude product was recrystallized from diethylether/hexane to give 335 mg (75% yield) of the title compound as a white solid.

후처리

  1. customwas put in the refrigerator overnight
  2. extractionthe reaction mixture was extracted twice with DCM
  3. washwashed with a 10% HCl solution
  4. additiontreated with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated to dryness
  8. customThe crude product was recrystallized from diethylether/hexane

출처 및 근거

ORD 기록
ord-077d38408ade483397030dde5c3e8879
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07947693B2

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