Trichloromethanesulfenyl chloride → HCID 13093902, compound

HRID 1660166Notes

Reaction equation

HRID 1660166 reaction equation
[OH-].[Na+].[C:3]([C:5]1[C:6](=[O:22])[NH:7][C:8](=[O:21])[N:9]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)[CH:10]=1)#[N:4].[Cl:23][C:24]([Cl:28])([Cl:27])[S:25]Cl>O.ClCCl>[C:3]([C:5]1[C:6](=[O:22])[N:7]([S:25][C:24]([Cl:28])([Cl:27])[Cl:23])[C:8](=[O:21])[N:9]([C:11]2[CH:12]=[CH:13][C:14]([C:17]([F:20])([F:18])[F:19])=[CH:15][CH:16]=2)[CH:10]=1)#[N:4]

Participants

6

Reactant 3

HCID 11666Trichloromethanesulfenyl chlorideHCID 14798Sodium HydroxideHCID 13014425HCID 13014425, compound

Product 1

HCID 13093902HCID 13093902, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent3×

Procedure

To 290 mg of NaOH in 15 ml of water, cooled in an ice bath, is added 1.0 g (3.56 mol) of 5-cyano-1-(4-trifluoromethylphenyl)uracil. Then 15 ml of dichloromethane is added, followed by 0.725 ml of trichloromethanesulphenyl chloride in 1.5 ml of dichloromethane. The mixture is stirred for approximately 2 hours at 5°. Then dichloromethane and ice cold water are added and the layers separated. The organic phase is washed with ice cold water, dried over MgSO4 and evaporated. The product is taken up with ether, filtered and washed again with ether to yield 5-cyano-3-trichloromethanesulphenyl-1-(4-trifluoromethylphenyl)uracil, m.p. 167°-168.5°.

Workup

  1. customthe layers separated
  2. washThe organic phase is washed with ice cold water
  3. dry with materialdried over MgSO4
  4. customevaporated
  5. filtrationfiltered
  6. washwashed again with ether

Sources & evidence

ORD record
ord-e394cdac01ca466ca6d1462ef83cebab
Source dataset
uspto-grants-1981_12
Patent number
US04307098

Reaction notes

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