Dimethyl Sulfide → 2-Chloro-5-dimethylaminobenzyl chloride

HRID 2371779Notes

Reaction equation

HRID 2371779 reaction equation
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]

Participants

4

Reactant 3

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

Product 1

HCID 193886882-Chloro-5-dimethylaminobenzyl chloride

Conditions

Temperature
0 °C

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-997be84384b547d1b4c278b8eaeaa20c
Source dataset
uspto-grants-1992_03
Patent number
US05095129

Reaction notes

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