Trichloromethanesulfenyl chloride → 5-Cyano-3-trichloromethanesulfenyl-1-phenyluracil

HRID 2198633Notes

Reaction equation

[Na].[C:2]([C:4]1[C:5](=[O:17])[NH:6][C:7](=[O:16])[N:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:9]=1)#[N:3].ClC(Cl)(F)SCl.[Cl:24][C:25]([Cl:29])([Cl:28])[S:26]Cl>>[C:2]([C:4]1[C:5](=[O:17])[N:6]([S:26][C:25]([Cl:29])([Cl:28])[Cl:24])[C:7](=[O:16])[N:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:9]=1)#[N:3]

Participants

Reactant 4

HCID 11666Trichloromethanesulfenyl chloride

HCID 759261,1-Dichloro-1-fluoromethanesulfenyl chloride

HCID 2351052,4-Dioxo-1-phenyl-1,2,3,4-tetrahydropyrimidine-5-carbonitrile

HCID 5360545Sodium

Product 1

HCID 205196325-Cyano-3-trichloromethanesulfenyl-1-phenyluracil

Procedure

The sodium salt of 5-cyano-1-phenyluracil is reacted with each of dichlorofluoromethanesulfenyl chloride and trichloromethanesulfenyl chloride following the procedure of Example 1 to yield 5-cyano-3-dichlorofluoromethanesulfenyl-1-phenyluracil and 5-cyano-3-trichloromethanesulfenyl-1-phenyluracil, respectively.

Sources & evidence

ORD record: ord-827996e4c0044216a7627299f4bc947f
Source dataset: uspto-grants-1982_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04358591

Reaction notes

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