Urea → 6-(3,4-dimethoxyphenyl)-2,4(1H,3H)-pyrimidinedione

HRID 65142Notes

Reaction equation

[C:1]([CH2:13][C:14]([O:16]CC)=O)(=O)[C:2]1[CH:11]=[CH:10][C:7]([O:8][CH3:9])=[C:4]([O:5][CH3:6])[CH:3]=1.[NH2:19][C:20]([NH2:22])=[O:21]>Cl.C(O)C>[CH3:6][O:5][C:4]1[CH:3]=[C:2]([C:1]2[NH:22][C:20](=[O:21])[NH:19][C:14](=[O:16])[CH:13]=2)[CH:11]=[CH:10][C:7]=1[O:8][CH3:9]

Participants

Conditions

Temperature: 120 °C

Procedure

To a mixture of ethyl veratroylacetate (45 g) and urea (11.7 g) were added conc. hydrochloric acid (5 drops) and ethanol (5 ml). The mixture was heated at 120° C. for 16 hours under reduced pressure. To the residue was added another conc. hydrochloric acid (5 drops) and ethanol (5 ml) and the mixture was heated again at 150° C. for 2 hours under reduced pressure. The resulting residue was washed successively with ethyl acetate, ethanol and isopropyl ether to give 6-(3,4-dimethoxyphenyl)-2,4(1H,3H)-pyrimidinedione (12.2 g).

Workup

temperaturethe mixture was heated again at 150° C. for 2 hours under reduced pressure
washThe resulting residue was washed successively with ethyl acetate, ethanol and isopropyl ether

Sources & evidence

ORD record: ord-4a23997972c74f00bc6998ce0427c2b5
Source dataset: uspto-grants-1986_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04612376

Reaction notes

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