(NE)-N-[4-oxo-3-(1H-1,2,4-triazol-5-ylsulfanyl)naphthalen-1-ylidene]thiophene-2-sulfonamide → N-(4-hydroxy-3-(1-methyl-1H-tetrazol-5-ylthio)naphthalen-1-yl)thiophene-2-sulfonamide

HRID 1258391Notes

Reaction equation

HRID 1258391 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([NH:12][S:13]([C:16]2[S:17][CH:18]=[CH:19][CH:20]=2)(=[O:15])=[O:14])=[CH:4][C:3]=1[S:21][C:22]1[N:26]([CH3:27])[N:25]=[N:24][N:23]=1.N1C(SC2C(=O)C3C(=CC=CC=3)/C(=N/S(C3SC=CC=3)(=O)=O)/C=2)=NC=N1>>[NH:23]1[C:22]([S:21][C:3]2[CH:4]=[C:5]([NH:12][S:13]([C:16]3[S:17][CH:18]=[CH:19][CH:20]=3)(=[O:15])=[O:14])[C:6]3[C:11]([C:2]=2[OH:1])=[CH:10][CH:9]=[CH:8][CH:7]=3)=[N:26][CH:27]=[N:24]1.[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([NH:12][S:13]([C:16]2[S:17][CH:18]=[CH:19][CH:20]=2)(=[O:15])=[O:14])=[CH:4][C:3]=1[S:21][C:22]1[N:26]([CH3:27])[N:25]=[N:24][N:23]=1

Participants

4

Reactant 2

HCID 44654329(NE)-N-[4-oxo-3-(1H-1,2,4-triazol-5-ylsulfanyl)naphthalen-1-ylidene]thiophene-2-sulfonamideHCID 135895396N-(4-hydroxy-3-(1-methyl-1H-tetrazol-5-ylthio)naphthalen-1-yl)thiophene-2-sulfonamide

Product 2

HCID 2133817N-[4-hydroxy-3-(1H-1,2,4-triazol-3-ylsulfanyl)naphthalen-1-yl]thiophene-2-sulfonamideHCID 135895396N-(4-hydroxy-3-(1-methyl-1H-tetrazol-5-ylthio)naphthalen-1-yl)thiophene-2-sulfonamideYield 100%

Procedure

N-(3-(1H-1,2,4-triazol-5-ylthio)-4-hydroxynaphthalen-1-yl)thiophene-2-sulfonamide (14e) was prepared according to the procedure for 14d except using (E)-N-(3-(1H-1,2,4-triazol-5-ylthio)-4-oxonaphthalen-1(4H)-ylidene)thiophene-2-sulfonamide (13e), which afforded the title compound 20 mg (100%) as a white solid, m.p.: 180° C. (dec.).

Sources & evidence

ORD record
ord-b3dc6b6db04f48e4946e4fa9d7230149
Source dataset
uspto-grants-2013_06
Patent number
US08466157B2

Reaction notes

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