Cyclohexene → 1-Chloromethyl-5-chloropyrimidin-2-one

HRID 247062

Reaction equation

HRID 247062 reaction equation
S(Cl)([Cl:4])(=O)=O.ClC1C=CC(S[CH2:14][N:15]2[CH:20]=[C:19]([Cl:21])[CH:18]=[N:17][C:16]2=[O:22])=CC=1.C1CCCCC=1>ClCCl>[Cl:4][CH2:14][N:15]1[CH:20]=[C:19]([Cl:21])[CH:18]=[N:17][C:16]1=[O:22]

Participants

5

Reactant 3

HCID 8079CyclohexeneHCID 24648Sulfuryl chlorideHCID 42952761-(4-Chlorophenylsulfenyl)methyl-5-chloropyrimidin-2-one

Product 1

HCID 201613341-Chloromethyl-5-chloropyrimidin-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

Sulphuryl chloride (3.0 mmol) in dry dichloromethane (10.0 ml) was added to 1-(4-chlorophenylsulphenyl) methyl-5-chloropyrimidin-2-one (see Example 2) (3.0 mmol) in dry dichlormethane 30.0 ml) at -30° C. for 3 mins. The mixture was stirred at -25° C. for 50 mins before cyclohexene (3.5 mmol) in dry dichloromethane (10 ml) was added. After stirring for 15 mins the mixture was filtered, evaporated and the residue washed three times with Pet. ether. Insoluble 1-chloromethyl-5-chloropyrimidin-2-one (0.45 g), 84% was used in Example 31 without further purification.

Workup

  1. additionwas added
  2. filtrationwas filtered
  3. customevaporated
  4. washthe residue washed three times with Pet. ether
  5. customInsoluble 1-chloromethyl-5-chloropyrimidin-2-one (0.45 g), 84% was used in Example 31 without further purification

Sources & evidence

ORD record
ord-d75c67c27b92457c97baa372c3f2dee8
Source dataset
uspto-grants-1987_11
Patent number
US04705791

Linked notes

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