Thionyl Chloride → HCID 19855598, compound

HRID 1650002Notes

Reaction equation

HRID 1650002 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]([CH2:17][CH:18](O)[CH3:19])[C:14](=[O:16])[CH3:15]>C1C=CC=CC=1>[CH3:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH3:12])[C:7]=1[N:13]([CH2:17][CH:18]([Cl:3])[CH3:19])[C:14](=[O:16])[CH3:15]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 19855576HCID 19855576, compound

Product 1

HCID 19855598HCID 19855598, compoundYield 81.9%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

6.5 ml (10.76 g, 90.4 mmoles) of thionyl chloride are added dropwise, within 20 minutes, to a solution of 20 g (90.4 mmoles) of 1[N-(2,6-dimethylphenyl)-acetamido]-2-propanol in 200 ml of benzene, and the mixture is boiled until the gas evolution ceases (for about 0.25 hours). The mixture is cooled, the solvent is evaporated under reduced pressure, and the oily residue is distilled under reduced pressure. 17.75 g (81.9%) of 1-[N-(2,6-dimethylphenyl)-acetamido]-2-chloro-propane are obtained; b.p.: 138°-140° C./93.3 Pa, m.p.: 41°-42° C.

Workup

  1. customis boiled until the gas evolution ceases (for about 0.25 hours)
  2. temperatureThe mixture is cooled
  3. customthe solvent is evaporated under reduced pressure
  4. distillationthe oily residue is distilled under reduced pressure

Sources & evidence

ORD record
ord-edbb99ea9b6246d4a70aab238c628a77
Source dataset
uspto-grants-1990_05
Patent number
US04922021

Reaction notes

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