2-Chloro-4-{[(4-methylphenyl)sulfonyl]azamethylene}naphthalen-1-one → (NE)-N-[3-(1-methyltetrazol-5-yl)sulfanyl-4-oxonaphthalen-1-ylidene]-4-phenylbenzenesulfonamide

HRID 1258405Notes

Reaction equation

HRID 1258405 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.ClC1C(=O)C2C(=CC=CC=2)/C(=N/S(C2C=CC(C)=CC=2)(=O)=O)/C=1>>[CH3:29][C:26]1[CH:27]=[CH:28][C:23]([S:20](/[N:19]=[C:10]2\[CH:9]=[C:8]([S:7][C:6]3[N:2]([CH3:1])[N:3]=[N:4][N:5]=3)[C:17](=[O:18])[C:16]3[C:11]\2=[CH:12][CH:13]=[CH:14][CH:15]=3)(=[O:21])=[O:22])=[CH:24][CH:25]=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

4

Reactant 2

HCID 57179882-Chloro-4-{[(4-methylphenyl)sulfonyl]azamethylene}naphthalen-1-oneHCID 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 96.1%HCID 46908381(NE)-4-methyl-N-[3-(1-methyltetrazol-5-yl)sulfanyl-4-oxonaphthalen-1-ylidene]benzenesulfonamide

Procedure

(E)-4-methyl-N-(3-(1-methyl-1H-tetrazol-5-ylthio)-4-oxonaphthalen-1(4H)-ylidene)benzenesulfonamide (13ad) was prepared according to the procedure for 13x except using 12i, affording 81.8 mg (96.1%) title compound as a yellow solid.

Sources & evidence

ORD record
ord-713f6926dd0d46958c812e07fea92160
Source dataset
uspto-grants-2013_06
Patent number
US08466157B2

Reaction notes

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