2-{[1-Hydroxy-4-(thiophene-2-sulfonamido)naphthalen-2-yl]sulfanyl}acetic acid → [(4-{[(4-Chlorophenyl)sulfonyl]amino}-1-hydroxy-2-naphthyl)thio]acetic acid

HRID 1186676Notes

Reaction equation

HRID 1186676 reaction equation
OC1C2C(=CC=CC=2)C(NS(C2SC=CC=2)(=O)=O)=CC=1[S:21][CH2:22][C:23]([OH:25])=[O:24].[Cl:26][C:27]1[CH:32]=[CH:31][C:30]([S:33](/[N:36]=[C:37]2\[CH:38]=[C:39](Cl)[C:40](=[O:47])[C:41]3[C:46]\2=[CH:45][CH:44]=[CH:43][CH:42]=3)(=[O:35])=[O:34])=[CH:29][CH:28]=1>>[Cl:26][C:27]1[CH:32]=[CH:31][C:30]([S:33]([NH:36][C:37]2[C:46]3[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=3)[C:40]([OH:47])=[C:39]([S:21][CH2:22][C:23]([OH:25])=[O:24])[CH:38]=2)(=[O:35])=[O:34])=[CH:29][CH:28]=1

Participants

3

Reactant 2

HCID 15826052-{[1-Hydroxy-4-(thiophene-2-sulfonamido)naphthalen-2-yl]sulfanyl}acetic acidHCID 96012334-chloro-N-(3-chloro-4-oxo-1(4H)-naphthalenylidene)benzenesulfonamide

Product 1

HCID 1309516[(4-{[(4-Chlorophenyl)sulfonyl]amino}-1-hydroxy-2-naphthyl)thio]acetic acid

Procedure

5.2.58 2-(4-(4-chlorophenylsulfonamido)-1-hydroxynaphthalen-2-ylthio)acetic acid (14p) was prepared according to the procedure of procedure B for 10a except using (E)-4-chloro-N-(3-chloro-4-oxonaphthalen-1(4H)-ylidene)-benzene sulfonamide (12e), which afforded the title compound 57.7 mg (68.4%) as a white solid, m.p.: 158-160° C.

Sources & evidence

ORD record
ord-3231df25f93549aa886f207f4e5f555a
Source dataset
uspto-grants-2014_03
Patent number
US08673910B2

Reaction notes

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