Thionyl Chloride → HCID 19855553, compound

HRID 1649993Notes

Reaction equation

HRID 1649993 reaction equation
S(Cl)([Cl:3])=O.[CH3:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH3:12])[C:7]=1[N:13]([CH2:22][CH:23](O)[CH3:24])[C:14](=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C1C=CC=CC=1>[CH3:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH3:12])[C:7]=1[N:13]([CH2:22][CH:23]([Cl:3])[CH3:24])[C:14](=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 19855561HCID 19855561, compound

Product 1

HCID 19855553HCID 19855553, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

4.65 ml (7.7 g, 65 mmoles) of thionyl chloride are added dropwise, at room temperature, to a solution of 14.2 g (50 mmoles) of 1-[N-(2,6-dimethylphenyl)-benzamido]-2-propanol in 100 ml of dry benzene, and the mixture is boiled then for 45 minutes. The solvent is evaporated under reduced pressure, and 30 ml of benzene is distilled off from the residue in order to remove the traces of thionyl chloride. This latter operation is repeated. The solid residue is triturated with n-hexane, the crystalline product is filtered off, washed with n-hexane and dried. 14.3 g (95%) of 1-[N-(2,6-dimethylphenyl)-benzamido]-2-chloro-propane are obtained as a white, crystalline substance; m.p.: 106°-109° C.

Workup

  1. customThe solvent is evaporated under reduced pressure, and 30 ml of benzene
  2. distillationis distilled off from the residue in order
  3. customto remove the traces of thionyl chloride
  4. customThe solid residue is triturated with n-hexane
  5. filtrationthe crystalline product is filtered off
  6. washwashed with n-hexane
  7. customdried

Sources & evidence

ORD record
ord-ca33d03d616b4e979dfaebddbe45e84b
Source dataset
uspto-grants-1990_05
Patent number
US04922021

Reaction notes

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