(NE)-N-(3-ethylsulfanyl-4-oxonaphthalen-1-ylidene)thiophene-2-sulfonamide → N-(4-hydroxy-3-(1-methyl-1H-tetrazol-5-ylthio)naphthalen-1-yl)thiophene-2-sulfonamide

HRID 1258392Notes

Reaction equation

HRID 1258392 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.[CH2:28]([S:30][C:31]1[C:40](=[O:41])[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)/[C:33](=[N:42]/[S:43]([C:46]2[S:47][CH:48]=[CH:49][CH:50]=2)(=[O:45])=[O:44])/[CH:32]=1)[CH3:29]>>[CH2:28]([S:30][C:31]1[CH:32]=[C:33]([NH:42][S:43]([C:46]2[S:47][CH:48]=[CH:49][CH:50]=2)(=[O:44])=[O:45])[C:34]2[C:39]([C:40]=1[OH:41])=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH3:29].[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 46908089(NE)-N-(3-ethylsulfanyl-4-oxonaphthalen-1-ylidene)thiophene-2-sulfonamideHCID 135895396N-(4-hydroxy-3-(1-methyl-1H-tetrazol-5-ylthio)naphthalen-1-yl)thiophene-2-sulfonamide

Product 2

HCID 46908186N-(3-(ethylthio)-4-hydroxynaphthalen-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-(ethylthio)-4-hydroxynaphthalen-1-yl)thiophene-2-sulfonamide (14j) was prepared according to the procedure for 14d except using (E)-N-(3-ethylthio-4-oxonaphthalen-1(4H)-ylidene)thiophene-2-sulfonamide (13j), which afforded the title compound 14 mg (100%) as a grey solid, m.p.: ° C.

Sources & evidence

ORD record
ord-9e885f11c8d84d2dbe64937fe0e4deea
Source dataset
uspto-grants-2013_06
Patent number
US08466157B2

Reaction notes

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