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

HRID 1982552

Reaction equation

HRID 1982552 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 (0.45g), 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 (0.45g), 84% was used in Example 31 without further purification

Sources & evidence

ORD record
ord-bb22960df29948dab85e7f975306220b
Source dataset
uspto-grants-1986_06
Patent number
US04596870

Linked notes

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