Water → 3-(1-Chloroethyl)benzamide

HRID 60524ノート

反応式

HRID 60524 の反応式
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]

参加物

6

反応物 4

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

生成物 1

HCID 666233683-(1-Chloroethyl)benzamide収率 75%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-8b1e0e37f0494fc1bfa468993a4babe8
出典データセット
uspto-grants-2016_09
特許番号
US09440992B2

反応ノート

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