Dichloromethane → HCID 13093901, compound

HRID 2198622Notes

Reaction equation

HRID 2198622 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 sulfenyl 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 sulfate, filtered and stripped. The residue is triturated with ether/pentane, filtered and dried to obtain the crude product, which is then purified by crystallization to yield 5-cyano-1-(2,6-dimethylphenyl)-3-trichloromethanesulfenyluracil, m.p. 223°-225.5°.

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 sulfate
  4. filtrationfiltered
  5. customThe residue is triturated with ether/pentane
  6. filtrationfiltered
  7. customdried
  8. customto obtain the crude product, which
  9. customis then purified by crystallization

Sources & evidence

ORD record
ord-4bda2d080d784d7ba2a83d5ce9d4b282
Source dataset
uspto-grants-1982_11
Patent number
US04358591

Reaction notes

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