(NE)-3,4-dichloro-N-(3-chloro-4-oxonaphthalen-1-ylidene)benzenesulfonamide → (NE)-N-[3-(1-methyltetrazol-5-yl)sulfanyl-4-oxonaphthalen-1-ylidene]-4-phenylbenzenesulfonamide

HRID 1258408Notes

Reaction equation

HRID 1258408 reaction equation
[CH3:1][N:2]1[C:6]([S:7][C:8]2[C:17](=[O:18])[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)/[C:10](=[N:19]/[S:20]([C:23]3[CH:28]=[CH:27][C:26]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)=[CH:25][CH:24]=3)(=[O:22])=[O:21])/[CH:9]=2)=[N:5][N:4]=[N:3]1.[Cl:35][C:36]1[CH:37]=[C:38]([S:43](/[N:46]=[C:47]2\[CH:48]=[C:49](Cl)[C:50](=[O:57])[C:51]3[C:56]\2=[CH:55][CH:54]=[CH:53][CH:52]=3)(=[O:45])=[O:44])[CH:39]=[CH:40][C:41]=1[Cl:42].SC1N=CNN=1>>[NH:4]1[CH:1]=[N:2][C:6]([S:7][C:49]2[C:50](=[O:57])[C:51]3[C:56](=[CH:55][CH:54]=[CH:53][CH:52]=3)/[C:47](=[N:46]/[S:43]([C:38]3[CH:39]=[CH:40][C:41]([Cl:42])=[C:36]([Cl:35])[CH:37]=3)(=[O:45])=[O:44])/[CH:48]=2)=[N:5]1.[CH3:1][N:2]1[C:6]([S:7][C:8]2[C:17](=[O:18])[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)/[C:10](=[N:19]/[S:20]([C:23]3[CH:28]=[CH:27][C:26]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)=[CH:25][CH:24]=3)(=[O:21])=[O:22])/[CH:9]=2)=[N:5][N:4]=[N:3]1

Participants

5

Reactant 3

HCID 46908284(NE)-3,4-dichloro-N-(3-chloro-4-oxonaphthalen-1-ylidene)benzenesulfonamideHCID 46908285(NE)-N-[3-(1-methyltetrazol-5-yl)sulfanyl-4-oxonaphthalen-1-ylidene]-4-phenylbenzenesulfonamideHCID 178527894HCID 178527894, compound

Product 2

HCID 46908285(NE)-N-[3-(1-methyltetrazol-5-yl)sulfanyl-4-oxonaphthalen-1-ylidene]-4-phenylbenzenesulfonamideYield 29.9%HCID 178516927HCID 178516927, compound

Procedure

(E)-N-(3-(1H-1,2,4-triazol-3-ylthio)-4-oxonaphthalen-1(4H)-ylidene)-3,4-dichlorobenzenesulfonamide (13ag) was prepared according to the procedure for 13x except using 12g and 3-mercapto-1,2,4-triazole, affording 27.8 mg (29.9%) title compound as a yellow solid.

Sources & evidence

ORD record
ord-31595a2fa4514d53940fa950cac3371f
Source dataset
uspto-grants-2013_06
Patent number
US08466157B2

Reaction notes

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