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

HRID 2198627Notes

Reaction equation

HRID 2198627 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]>O.ClCCl.[Cl-].C([N+](CC)(CC)CC1C=CC=CC=1)C>[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

7

Reactant 3

HCID 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 3

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

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-tetrachloroethanesulfenyl 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°, after which time 50 mg of triethylbenzylammonium chloride is added and stirring is continued for another 30 min at 4°. The aqueous layer is separated and discarded. The dichloromethane solution is dried and stripped at aspirator pressure. The unreacted sulfenyl 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-tetrachloroethanesulfenyl)uracil, m.p. 180°-183°.

Workup

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

Sources & evidence

ORD record
ord-c95dead7088345638bfaa9d33b7c8b4d
Source dataset
uspto-grants-1982_11
Patent number
US04358591

Reaction notes

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