Dimethyl Sulfide → 2-Chloro-5-dimethylaminobenzyl chloride

HRID 1757616ノート

反応式

HRID 1757616 の反応式
CSC.[Cl:4][C:5]1[CH:12]=[CH:11][C:10]([N:13]([CH3:15])[CH3:14])=[CH:9][C:6]=1[CH2:7]O.C(Cl)[Cl:17]>>[Cl:4][C:5]1[CH:12]=[CH:11][C:10]([N:13]([CH3:15])[CH3:14])=[CH:9][C:6]=1[CH2:7][Cl:17]

参加物

4

反応物 3

HCID 1068Dimethyl SulfideHCID 6344DichloromethaneHCID 54011893[2-Chloro-5-(dimethylamino)phenyl]methanol

生成物 1

HCID 193886882-Chloro-5-dimethylaminobenzyl chloride

反応条件

温度
0 °C

実験手順

23.8 g of N-chlorosuccinimide provided in 600 ml of absolute methylene chloride is cooled to 0° C. and is slowly mixed with 15.6 ml of dimethyl sulfide. Thereafter the suspension thus produced is cooled to -30° C. and carefully mixed with 20 g of 2-chloro-5-dimethylaminobenzyl alcohol. The reaction mixture is then warmed to 0° C. and stirred at this temperature for 3 hours. Thereafter the mixture is diluted with methylene chloride and poured into ice water. The organic phase is separated, washed with saturated sodium chloride solution, dried over sodium sulfate solution and concentrated in vacuo. The residue is chromatographed with hexane over aluminum oxide (neutral, stage III). A yield of 17.2 g of 2-chloro-5-dimethylaminobenzyl chloride is obtained.

後処理

  1. customThereafter the suspension thus produced
  2. temperatureis cooled to -30° C.
  3. temperatureThe reaction mixture is then warmed to 0° C.
  4. customThe organic phase is separated
  5. washwashed with saturated sodium chloride solution
  6. dry with materialdried over sodium sulfate solution
  7. concentrationconcentrated in vacuo
  8. customThe residue is chromatographed with hexane over aluminum oxide (neutral, stage III)

出典と根拠

ORDレコード
ord-d30edf21989e48ffb136b102279c625f
出典データセット
uspto-grants-1995_08
特許番号
US05446178

反応ノート

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