Thionyl Chloride → HCID 12674604, compound

HRID 596467Notes

Reaction equation

HRID 596467 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:12][CH:11]([CH3:13])[N:10]([CH:14]([CH2:16]O)[CH3:15])[C:9]2=[O:18])=[CH:4][CH:3]=1.O=S(Cl)[Cl:21]>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:12][CH:11]([CH3:13])[N:10]([CH:14]([CH3:15])[CH2:16][Cl:21])[C:9]2=[O:18])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 12674602HCID 12674602, compound

Product 1

HCID 12674604HCID 12674604, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 16 g. of 1-(p-chlorophenyl)-3-(1-(hydroxymethyl)ethyl)-4-methyl-2-imidazolidinone in 400 ml. of anhydrous chloroform, 14.5 g. of SOCl2 is added dropwise with stirring while the temperature is maintained at 0° C. The mixture is then refluxed for 45 minutes, concentrated under vacuum and taken up with benzene, then evaporated to dryness again, yielding 15.1 grams (94%) of the title compound, m.p. 70°-72° C. (from diisopropyl ether). The corresponding m-chlorophenyl-substituted compound is prepared in the same way. Yield 97%, b.p. 200° C./0.5 mm Hg.

Workup

  1. temperatureThe mixture is then refluxed for 45 minutes
  2. concentrationconcentrated under vacuum
  3. customevaporated to dryness again

Sources & evidence

ORD record
ord-f5644c9186be45f1b9adf60775f67dff
Source dataset
uspto-grants-1977_03
Patent number
US04011238

Reaction notes

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