Chloride → 5-Chloro-6-(chloromethyl)-1,2,3,4-tetrahydropyrimidine-2,4-dione

HRID 1358226Notes

Reaction equation

HRID 1358226 reaction equation
[Cl-:1].[Cl:2][CH2:3][C:4]1[NH:9][C:8](=[O:10])[NH:7][C:6](=[O:11])[CH:5]=1>C(O)(=O)C>[Cl:1][C:5]1[C:6](=[O:11])[NH:7][C:8](=[O:10])[NH:9][C:4]=1[CH2:3][Cl:2]

Participants

4

Reactant 2

HCID 312ChlorideHCID 732736-(Chloromethyl)-2,4(1H,3H)-pyrimidinedione

Product 1

HCID 41710565-Chloro-6-(chloromethyl)-1,2,3,4-tetrahydropyrimidine-2,4-dioneYield 92%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Sulfulyl chloride (120 ml) was added dropwise to a suspension of 163 g of 6-chloromethyluracil in 500 ml of acetic acid at room temperature for 20 minutes and stirred at the same temperature for 3 hours. The reaction mixture was poured into ice water (500 ml) and the resulting crystals were collected by filtration to give 182.3 g of 5-chloro-6-chloromethyluracil (yield 92%). The physical properties of this compound are as follows:

Workup

  1. filtrationthe resulting crystals were collected by filtration

Sources & evidence

ORD record
ord-220861fb00c94a77b73791bb53c5297b
Source dataset
uspto-grants-2003_07
Patent number
US06596720B1

Reaction notes

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