Acetic Anhydride → 1-(4-Chloro-2-methylphenyl)-3-methyl-1,3-diazinane-2,4-dione

HRID 280105Notes

Reaction equation

HRID 280105 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]([N:12]([CH3:18])[CH2:13][CH2:14][C:15](O)=O)=[O:11].C(OC(=O)C)(=[O:21])C>>[CH3:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[N:9]1[CH2:15][CH2:14][C:13](=[O:21])[N:12]([CH3:18])[C:10]1=[O:11]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 23321825HCID 23321825, compound

Product 1

HCID 30598851-(4-Chloro-2-methylphenyl)-3-methyl-1,3-diazinane-2,4-dioneYield 24.1%

Procedure

At first, 8.0 g (0.03 moles) of N-(2-methyl-4-chlorophenylcarbamoyl)-N-methyl-β-alanine was added to 250 ml of acetic anhydride, and the mixture was refluxed with heating for 2.5 hours. Acetic anhydride was removed therefrom by distillation under reduced pressure, and precipitated crystals were recrystallized from 60 ml of ethyl acetate and 150 ml of n-hexane, whereby 1.8 g of the desired compound was obtained as crystals having a melting point of 120° to 127° C. (yield: 24.1%).

Workup

  1. temperaturethe mixture was refluxed
  2. temperaturewith heating for 2.5 hours
  3. customAcetic anhydride was removed
  4. distillationby distillation under reduced pressure
  5. customprecipitated crystals
  6. customwere recrystallized from 60 ml of ethyl acetate and 150 ml of n-hexane

Sources & evidence

ORD record
ord-eed117cb30d74e52afcb95a3f8d18749
Source dataset
uspto-grants-1986_05
Patent number
US04588729

Reaction notes

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