(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 1258401Notes

Reaction equation

HRID 1258401 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]>>[Cl:35][C:36]1[CH:37]=[C:38]([S:43](/[N:46]=[C:47]2\[CH:48]=[C:49]([S:7][C:6]3[N:2]([CH3:1])[N:3]=[N:4][N:5]=3)[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].[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

4

Reactant 2

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-phenylbenzenesulfonamide

Product 2

HCID 46908285(NE)-N-[3-(1-methyltetrazol-5-yl)sulfanyl-4-oxonaphthalen-1-ylidene]-4-phenylbenzenesulfonamideYield 98.5%HCID 46908378(NE)-3,4-dichloro-N-[3-(1-methyltetrazol-5-yl)sulfanyl-4-oxonaphthalen-1-ylidene]benzenesulfonamide

Procedure

(E)-3,4-dichloro-N-(3-(1-methyl-1H-tetrazol-5-ylthio)-4-oxonaphthalen-1(4H)-ylidene)benzenesulfonamide (13z) was prepared according to the procedure for 13x except using 12g, affording 94.7 mg (98.5%) title compound as a yellow solid.

Sources & evidence

ORD record
ord-00344ce8724d4b41ae726a87219af8d9
Source dataset
uspto-grants-2013_06
Patent number
US08466157B2

Reaction notes

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