1-(2-Methylphenyl)-2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-carbonitrile → HCID 20519634, compound

HRID 2198632Notes

Reaction equation

HRID 2198632 reaction equation
[Cl:1][C:2]([S:6]Cl)=[C:3]([Cl:5])[Cl:4].[Na].[C:9]([C:11]1[C:12](=[O:26])[NH:13][C:14](=[O:25])[N:15]([C:17]2[C:22]([CH3:23])=[CH:21][CH:20]=[CH:19][C:18]=2[CH3:24])[CH:16]=1)#[N:10].[C:27]([C:29]1[C:30](=[O:43])[NH:31][C:32](=[O:42])[N:33]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=2[CH3:41])[CH:34]=1)#[N:28].[C:44]([C:46]1[C:47](=[O:61])[NH:48][C:49](=[O:60])[N:50]([C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][C:53]=2[CH2:58][CH3:59])[CH:51]=1)#[N:45].[C:62]([C:64]1[C:65](=[O:81])[NH:66][C:67](=[O:80])[N:68]([C:70]2[C:75]([CH2:76][CH3:77])=[CH:74][CH:73]=[CH:72][C:71]=2[CH2:78][CH3:79])[CH:69]=1)#[N:63]>>[C:9]([C:11]1[C:12](=[O:26])[N:13]([S:6][C:2]([Cl:1])=[C:3]([Cl:5])[Cl:4])[C:14](=[O:25])[N:15]([C:17]2[C:22]([CH3:23])=[CH:21][CH:20]=[CH:19][C:18]=2[CH3:24])[CH:16]=1)#[N:10].[C:27]([C:29]1[C:30](=[O:43])[N:31]([S:6][C:2]([Cl:1])=[C:3]([Cl:5])[Cl:4])[C:32](=[O:42])[N:33]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=2[CH3:41])[CH:34]=1)#[N:28].[C:44]([C:46]1[C:47](=[O:61])[N:48]([S:6][C:2]([Cl:1])=[C:3]([Cl:5])[Cl:4])[C:49](=[O:60])[N:50]([C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][C:53]=2[CH2:58][CH3:59])[CH:51]=1)#[N:45].[C:62]([C:64]1[C:65](=[O:81])[N:66]([S:6][C:2]([Cl:1])=[C:3]([Cl:5])[Cl:4])[C:67](=[O:80])[N:68]([C:70]2[C:75]([CH2:76][CH3:77])=[CH:74][CH:73]=[CH:72][C:71]=2[CH2:78][CH3:79])[CH:69]=1)#[N:63]

Participants

10

Reactant 6

HCID 28232121-(2-Methylphenyl)-2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-carbonitrileHCID 5360545SodiumHCID 13014421HCID 13014421, compoundHCID 20519645HCID 20519645, compoundHCID 205196721,1,2-Trichloro-2-(chlorosulfanyl)etheneHCID 20519722HCID 20519722, compound

Product 4

HCID 20519634HCID 20519634, compoundHCID 20519678HCID 20519678, compoundHCID 20519696HCID 20519696, compoundHCID 20519708HCID 20519708, compound

Procedure

Following the procedure of Example 5, trichloroethenesulfenyl chloride is reacted with the sodium salt of each of 5-cyano-1-(2,6-dimethylphenyl)uracil, 5-cyano-1-(2-methylphenyl)uracil, 5-cyano-1-(2-ethylphenyl)uracil and 5-cyano-1-(2,6-diethylphenyl)uracil to yield 5-cyano-1-(2,6-dimethylphenyl)-3-trichloroethenesulfenyluracil, 5-cyano-1-(2-methylphenyl)-3-trichloroethenesulfenyluracil, 5-cyano-1-(2-ethylphenyl)-3-trichloroethenesulfenyluracil and 5-cyano-1-(2,6-diethylphenyl)-3-trichloroethenesulfenyluracil.

Sources & evidence

ORD record
ord-bbf6c891cc1c45778ffc1f015aab8426
Source dataset
uspto-grants-1982_11
Patent number
US04358591

Reaction notes

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