2-{[1-Hydroxy-4-(thiophene-2-sulfonamido)naphthalen-2-yl]sulfanyl}acetic acid → 2-(4-(4-Chlorophenylsulfonamido)-1-hydroxynaphthalen-2-ylthio)propanoic acid

HRID 1186681Notes

Reaction equation

HRID 1186681 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].[C:26](O)(=S)C(C)O.[Cl:32][C:33]1[CH:38]=[CH:37][C:36]([S:39](/[N:42]=[C:43]2\[CH:44]=[C:45](Cl)[C:46](=[O:53])[C:47]3[C:52]\2=[CH:51][CH:50]=[CH:49][CH:48]=3)(=[O:41])=[O:40])=[CH:35][CH:34]=1>>[Cl:32][C:33]1[CH:38]=[CH:37][C:36]([S:39]([NH:42][C:43]2[C:52]3[C:47](=[CH:48][CH:49]=[CH:50][CH:51]=3)[C:46]([OH:53])=[C:45]([S:21][CH:22]([CH3:26])[C:23]([OH:25])=[O:24])[CH:44]=2)(=[O:41])=[O:40])=[CH:35][CH:34]=1

Participants

4

Reactant 3

HCID 15826052-{[1-Hydroxy-4-(thiophene-2-sulfonamido)naphthalen-2-yl]sulfanyl}acetic acidHCID 96012334-chloro-N-(3-chloro-4-oxo-1(4H)-naphthalenylidene)benzenesulfonamideHCID 178473673HCID 178473673, compound

Product 1

HCID 446093092-(4-(4-Chlorophenylsulfonamido)-1-hydroxynaphthalen-2-ylthio)propanoic acid

Procedure

5.2.63 2-(4-(4-chlorophenylsulfonamido)-1-hydroxynaphthalen-2-ylthio)propanoic acid (14u) was prepared according to the procedure of procedure B for 10a except using thiolactic acid and (E)-4-chloro-N-(3-chloro-4-oxonaphthalen-1(4H)-ylidene)-benzenesulfonamide (12e), which afforded the title compound 41.3 mg (49%) as a white solid, m.p.: 177-179° C.

Sources & evidence

ORD record
ord-eb07eea74f934dbba37e37c2ac446d01
Source dataset
uspto-grants-2014_03
Patent number
US08673910B2

Reaction notes

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