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Thionyl Chloride → N-benzyl-2-chloro-N-methylethanamine

HRID 248845
ノート
印刷プレビュー

反応式

HRID 248845 の反応式
[CH2:1]([N:8]([CH3:12])[CH2:9][CH2:10]O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)([Cl:15])=O>ClCCl.CN(C)C=O>[CH2:1]([N:8]([CH2:9][CH2:10][Cl:15])[CH3:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 24386Thionyl ChlorideHCID 66876N-Benzyl-N-methylethanolamine

生成物 1

HCID 31968N-benzyl-2-chloro-N-methylethanamine収率 79.1%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide触媒HCID 6344Dichloromethane溶媒

実験手順

33 g of N-benzyl-N-methyl-2-aminoethanol were dissolved in 300 ml of dichloromethane. 48 g of thionyl chloride and 2 drops of dimethylformamide were added to the solution at 0° C. The reaction mixture was then heated under reflux for 6 hours. The reaction mixture was worked up by evaporating it to dryness and taking up the residue three times in 300 ml portions of toluene and again evaporating to dryness. The remaining residue was dissolved in dichloromethane and the N-benzyl-N-(2-chloroethyl)-N-methylamine hydrochloride was crystallized by addition of diethyl ether to the solution. The crystals (m.p. 142° C.-145° C.) were filtered out and dissolved in ice water. The solution was adjusted to alkaline pH 9 by addition of aqueous sodium hydroxide solution and then extracted with toluene. The organic phase was separated, dried over sodium sulfate, filtered and concentrated under reduced pressure. 29 g of N-benzyl-N-(2- chloroethyl)-N-methylamine were obtained as a residue.

後処理

  1. temperatureThe reaction mixture was then heated
  2. temperatureunder reflux for 6 hours
  3. customby evaporating it to dryness
  4. customagain evaporating to dryness
  5. dissolutionThe remaining residue was dissolved in dichloromethane
  6. customthe N-benzyl-N-(2-chloroethyl)-N-methylamine hydrochloride was crystallized by addition of diethyl ether to the solution
  7. filtrationThe crystals (m.p. 142° C.-145° C.) were filtered out
  8. dissolutiondissolved in ice water
  9. additionby addition of aqueous sodium hydroxide solution
  10. extractionextracted with toluene
  11. customThe organic phase was separated
  12. dry with materialdried over sodium sulfate
  13. filtrationfiltered
  14. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-ab2537e535ec47f8af68b8af48329d29
出典データセット
uspto-grants-1993_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05212173

反応ノート

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