ethanesulfenyl chloride → HCID 13326281, compound

HRID 544211Notes

Reaction equation

HRID 544211 reaction equation
[C:1]([C:3]1[N:8]([NH:9][C:10]2[C:15]([Cl:16])=[CH:14][C:13]([Cl:17])=[CH:12][C:11]=2[Cl:18])[C:7](=[O:19])[NH:6][C:5](=[O:20])[CH:4]=1)#[N:2].[CH2:21]([S:23]Cl)[CH3:22]>[OH-].[Na+].C(Cl)Cl>[C:1]([C:3]1[NH:8][C:7](=[O:19])[N:6]([S:23][CH2:21][CH3:22])[C:5](=[O:20])[C:4]=1[NH:9][C:10]1[C:11]([Cl:18])=[CH:12][C:13]([Cl:17])=[CH:14][C:15]=1[Cl:16])#[N:2].[C:1]([C:3]1[N:8]([N:9]([S:23][CH2:21][CH3:22])[C:10]2[C:11]([Cl:18])=[CH:12][C:13]([Cl:17])=[CH:14][C:15]=2[Cl:16])[C:7](=[O:19])[NH:6][C:5](=[O:20])[CH:4]=1)#[N:2]

Participants

6

Reactant 2

HCID 12275523ethanesulfenyl chlorideHCID 20459817HCID 20459817, compound

Product 2

HCID 13326281HCID 13326281, compoundHCID 53938821HCID 53938821, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 14798Sodium HydroxideSolvent

Procedure

In the same manner as above, 6-cyano-1-(2,4,6-trichloroanilino)-2,4-pyrimidinedione in aqueous sodium hydroxide is reacted with ethylsulfenyl chloride in methylene chloride, followed by chromatography yields the compounds 6-cyano-3-ethylthio-(2,4,6-trichloroanilino)-2,4-pyrimidinedione and 6-cyano-1-(N-ethylthio-2,4,6-trichloroanilino)-2,4-pyrimidinedione.

Sources & evidence

ORD record
ord-7899167be59b4ff08df6bcbd019a7112
Source dataset
uspto-grants-1984_05
Patent number
US04448961

Reaction notes

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