Trichloromethanesulfenyl chloride → HCID 13326271, compound

HRID 648174Notes

Reaction equation

HRID 648174 reaction equation
[C:1]([C:3]1[N:8]([NH:9][C:10]2[C:15]([CH3:16])=[CH:14][CH:13]=[CH:12][C:11]=2[CH3:17])[C:7](=[O:18])[NH:6][C:5](=[O:19])[CH:4]=1)#[N:2].[OH-].[Na+].[Cl:22][C:23]([Cl:27])([Cl:26])[S:24]Cl>C(Cl)Cl>[C:1]([C:3]1[N:8]([NH:9][C:10]2[C:15]([CH3:16])=[CH:14][CH:13]=[CH:12][C:11]=2[CH3:17])[C:7](=[O:18])[N:6]([S:24][C:23]([Cl:27])([Cl:26])[Cl:22])[C:5](=[O:19])[CH:4]=1)#[N:2].[C:1]([C:3]1[N:8]([N:9]([S:24][C:23]([Cl:27])([Cl:26])[Cl:22])[C:10]2[C:15]([CH3:16])=[CH:14][CH:13]=[CH:12][C:11]=2[CH3:17])[C:7](=[O:18])[NH:6][C:5](=[O:19])[CH:4]=1)#[N:2]

Participants

6

Reactant 3

HCID 11666Trichloromethanesulfenyl chlorideHCID 14798Sodium HydroxideHCID 13326270HCID 13326270, compound

Product 2

HCID 13326271HCID 13326271, compoundHCID 13326272HCID 13326272, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 6-cyano-1-(2,6-dimethylanilino)-2,4-pyrimidinedione (50 mmol) and aqueous sodium hydroxide (50 mmol) is added 55 mmol of trichloromethylsulfenyl chloride in methylene chloride at 5° and with rapid stirring. When the pH of the mixture is 7-8, the reaction is complete. The layers are separated and the aqueous phase is discarded. The methylene chloride is removed, followed by washing with water and drying to yield a mixture of two crude products. Separation by chromatography on silica gel, eluting with acetone/hexane, gives the two final products, 6-cyano-1-(2,6-dimethylanilino)-3-trichloromethylthio-2,4-pyrimidinedione and 6-cyano-1-(2,6-dimethyl-N-trichloromethylthioanilino)-2,4-pyrimidinedione.

Workup

  1. customThe layers are separated
  2. customThe methylene chloride is removed
  3. washby washing with water
  4. customdrying
  5. customto yield
  6. additiona mixture of two crude products
  7. customSeparation by chromatography on silica gel
  8. washeluting with acetone/hexane

Sources & evidence

ORD record
ord-b953e2b01dd242b3b128d715f43721de
Source dataset
uspto-grants-1983_10
Patent number
US04411839

Reaction notes

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