Hydrochloric Acid → 5-Chlorouracil

Reaction equation

Cl.[Cl:2][C:3]1(C(OC)=O)[CH:8](O)[NH:7][C:6](=[O:10])[NH:5][C:4]1=[O:11]>>[Cl:2][C:3]1[C:4](=[O:11])[NH:5][C:6](=[O:10])[NH:7][CH:8]=1

Participants

Reactant 2

HCID 313Hydrochloric Acid

HCID 12890662Methyl 5-chloro-6-hydroxy-1,2,3,4,5,6-hexahydro-2,4-dioxopyrimidine-5-carboxylate

Product 1

HCID 157585-Chlorouracil

Procedure

In 15 ml. of concentrated hydrochloric acid, 345 mg. of methyl 5-chloro-6-hydroxy-1,2,3,4,5,6-hexahydro-2,4-dioxopyrimidine-5-carboxylate is heated under reflux for 15 hours. The reaction mixture is cooled with ice, whereupon 92 mg. of 5-chlorouracil is obtained as colorless prisms.

Workup

temperatureunder reflux for 15 hours
temperatureThe reaction mixture is cooled with ice, whereupon 92 mg

Sources & evidence

ORD record: ord-38903b307ce349258b3a3861a9e96bb1
Source dataset: uspto-grants-1982_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04329460

Reaction notes

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