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

HRID 1383337Notes

Reaction equation

HRID 1383337 reaction equation
[Cl:1][CH2:2][C:3]1[NH:8][C:7](=[O:9])[NH:6][C:5](=[O:10])[CH:4]=1.S(Cl)([Cl:14])(=O)=O>C(O)(=O)C>[Cl:14][C:4]1[C:5](=[O:10])[NH:6][C:7](=[O:9])[NH:8][C:3]=1[CH2:2][Cl:1]

Participants

4

Reactant 2

HCID 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

To a suspension of 6-chloromethyluracil (163 g) in acetic acid (500 ml), sulfuryl chloride (120 ml) was added dropwise at room temperature over 20 minutes, followed by stirring at the same temperature for 3 hours. The reaction mixture was poured into ice water (500 ml), and a crystallized matter was collected by filtration, whereby 182.3 g of the title compound were obtained (yield: 92%).

Workup

  1. additionwas added dropwise at room temperature over 20 minutes
  2. filtrationa crystallized matter was collected by filtration

Sources & evidence

ORD record
ord-ec2c496397a7421c9a8d7bc59d211889
Source dataset
uspto-grants-2001_07
Patent number
US06255314B1

Reaction notes

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