1,1,2,2-Tetrachloroethylsulfenyl chloride → 6-propyl-1H-pyrimidin-4-one;hydrochloride

HRID 328199Notes

Reaction equation

HRID 328199 reaction equation
S[C:2]1[N:7]=[C:6]([OH:8])[CH:5]=[C:4]([CH2:9][CH2:10][CH3:11])[N:3]=1.[Cl:12]C(Cl)(SCl)C(Cl)Cl>COCCOC>[ClH:12].[OH:8][C:6]1[CH:5]=[C:4]([CH2:9][CH2:10][CH3:11])[N:3]=[CH:2][N:7]=1

Participants

4

Reactant 2

HCID 144531,1,2,2-Tetrachloroethylsulfenyl chlorideHCID 178439476HCID 178439476, compound

Product 1

HCID 1784394686-propyl-1H-pyrimidin-4-one;hydrochloride

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

To a slurry of 5.0 g (0.029 mol) of 2-mercapto-4-hydroxy-6-propyl pyrimidine in 50 ml of 1,2-dimethoxyethane was added 6.9 g (0.029 mol) of 1,1,2,2-tetrachloroethylsulfenyl chloride. The resulting mixture was heated at the reflux temperature for 10 minutes, and then filtered while still hot. The solvent was removed by evaporation under reduced pressure to give 8.8 g of 1,1,2,2-tetrachloroethylsulfenylmercapto)-4-hydroxy-6-propyl pyrimidine hydrochloride having a melting point of 142°-144° C. Analysis was as follows: %Cl, calc., 43.8, found 43.0; %S, calc. 15.8, found 15.5.

Workup

  1. temperatureThe resulting mixture was heated at the reflux temperature for 10 minutes
  2. filtrationfiltered while still hot
  3. customThe solvent was removed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-96dae9673bb64a038e2e1928c5909d00
Source dataset
uspto-grants-1977_04
Patent number
US04016275

Reaction notes

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