Dichloromethane → 5-Cyano-1-(2,6-dimethylphenyl)-3-(1,1,2,2-tetrachloroethanesulfenyl)uracil

HRID 1660168Notes

Reaction equation

HRID 1660168 reaction equation
[OH-].[Na+].[C:3]([C:5]1[C:6](=[O:20])[NH:7][C:8](=[O:19])[N:9]([C:11]2[C:16]([CH3:17])=[CH:15][CH:14]=[CH:13][C:12]=2[CH3:18])[CH:10]=1)#[N:4].[Cl:21][C:22]([Cl:28])([S:26]Cl)[CH:23]([Cl:25])[Cl:24].ClCCl>O>[C:3]([C:5]1[C:6](=[O:20])[N:7]([S:26][C:22]([Cl:28])([Cl:21])[CH:23]([Cl:25])[Cl:24])[C:8](=[O:19])[N:9]([C:11]2[C:16]([CH3:17])=[CH:15][CH:14]=[CH:13][C:12]=2[CH3:18])[CH:10]=1)#[N:4]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 144531,1,2,2-Tetrachloroethylsulfenyl chlorideHCID 14798Sodium HydroxideHCID 13014421HCID 13014421, compound

Product 1

HCID 130939045-Cyano-1-(2,6-dimethylphenyl)-3-(1,1,2,2-tetrachloroethanesulfenyl)uracil

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To an ice cold solution of 1.60 g (0.04 mol) of NaOH in 45 ml of water is added 9.64 g (0.04 mol) of 5-cyano-1-(2,6-dimethylphenyl)uracil, obtained as in Example 1. After dissolution, 50 ml of ice cold dichloromethane is added, followed by a solution of 9.36 g (0.04 mol) of 1,1,2,2-tetrachloroethanesulphenyl chloride (prepared by the method of U.S. Pat. No. 3,395,180) in 15 ml. of dichloromethane. The mixture is stirred for 30 min at 4°. The aqueous layer is separated and discarded. The dichloromethane solution is dried and stripped at aspirator pressure. The unreacted sulphenyl chloride is then removed by trituration with pentane/dichloromethane (4:1). The resultant crude product is purified by slurrying at 30° in 60 ml of ethanol-free chloroform, allowed to cool to RT and filtered. To the filtrate is added hexane to the cloud point, and the mixture is then filtered to yield 5-cyano-1-(2,6-dimethylphenyl)-3-(1,1,2,2-tetrachloroethanesulphenyl)uracil, m.p. 180°-183°.

Workup

  1. customobtained as in Example 1
  2. additionis added
  3. customprepared by the method of U.S
  4. customThe aqueous layer is separated
  5. dry with materialThe dichloromethane solution is dried
  6. customThe unreacted sulphenyl chloride is then removed by trituration with pentane/dichloromethane (4:1)
  7. customThe resultant crude product is purified
  8. customby slurrying at 30° in 60 ml of ethanol-free chloroform
  9. filtrationfiltered
  10. additionTo the filtrate is added hexane to the cloud point
  11. filtrationthe mixture is then filtered

Sources & evidence

ORD record
ord-310512753cfe42359de2aae1ed7aafc9
Source dataset
uspto-grants-1981_12
Patent number
US04307098

Reaction notes

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