Dichloromethane → HCID 13093901, compound

HRID 1660163Notes

Reaction equation

HRID 1660163 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].ClCCl.[Cl:24][C:25]([Cl:29])([Cl:28])[S:26]Cl>O>[C:3]([C:5]1[C:6](=[O:20])[N:7]([S:26][C:25]([Cl:29])([Cl:28])[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 6344Dichloromethane2×HCID 11666Trichloromethanesulfenyl chlorideHCID 14798Sodium HydroxideHCID 13014421HCID 13014421, compound

Product 1

HCID 13093901HCID 13093901, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To an ice cold solution of 2.40 g of sodium hydroxide in 70 ml of water is added 14.46 g (0.06 mol) of 5-cyano-1-(2,6-dimethylphenyl)uracil. Then 100 ml of dichloromethane is added. To this mixture, at 5°, is added 6.6 ml (0.06 mol) of trichloromethane sulphenyl chloride in two volumes of dichloromethane. The mixture is stirred approximately 22 min at 5°. Then the phases are separated and the organic phase is washed with ice cold water. The dichloromethane solution is dried over magnesium sulphate, filtered and stripped. The residue is triturated with ether/petane, filtered and dried to obtain the crude product, which is then purified by crystallisation to yield 5-cyano-1-(2,6-dimethylphenyl)-3-trichloromethanesulphenyluracil, m.p. 223°-225°.

Workup

  1. customThen the phases are separated
  2. washthe organic phase is washed with ice cold water
  3. dry with materialThe dichloromethane solution is dried over magnesium sulphate
  4. filtrationfiltered
  5. customThe residue is triturated with ether/petane
  6. filtrationfiltered
  7. customdried
  8. customto obtain the crude product, which
  9. customis then purified by crystallisation

Sources & evidence

ORD record
ord-5a08c450fb624e30ac3a10ad8180b314
Source dataset
uspto-grants-1981_12
Patent number
US04307098

Reaction notes

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