Dimethyl Sulfide → 2-Chloro-5-dimethylaminobenzyl chloride

HRID 1757616노트

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HRID 1757616 반응식
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]

참가 물질

4

반응물 3

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

생성물 1

HCID 193886882-Chloro-5-dimethylaminobenzyl chloride

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온도
0 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-d30edf21989e48ffb136b102279c625f
출처 데이터셋
uspto-grants-1995_08
특허 번호
US05446178

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