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

HRID 1017500Notes

Reaction equation

HRID 1017500 reaction equation
S(Cl)([Cl:4])(=O)=O.[Cl:6][CH2:7][C:8]1[NH:13][C:12](=[O:14])[NH:11][C:10](=[O:15])[CH:9]=1.O>C(O)(=O)C>[Cl:4][C:9]1[C:10](=[O:15])[NH:11][C:12](=[O:14])[NH:13][C:8]=1[CH2:7][Cl:6]

Participants

5

Reactant 3

HCID 962WaterHCID 24648Sulfuryl chlorideHCID 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

Sulfuryl chloride (120 ml) was added dropwise to a suspension of 6-chloromethyluracil (163 g) in acetic acid (500 ml) over 20 minutes at room temperature, and the mixture was stirred for an additional 3 hours at room temperature. The resultant solution was poured into iced water (500 ml), and then precipitated crystals were collected through filtration, to there by obtain 182.3 g of 5-chloro-6-chloromethyluracil (92% yield).

Workup

  1. customprecipitated crystals
  2. filtrationwere collected through filtration, to there

Sources & evidence

ORD record
ord-61e4140b5be64e40835bc04847fcbbb0
Source dataset
uspto-grants-2002_11
Patent number
US06479500B1

Reaction notes

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