2-{[1-Hydroxy-4-(thiophene-2-sulfonamido)naphthalen-2-yl]sulfanyl}acetic acid → 2-(4-(5-Chlorothiophene-2-sulfonamido)-1-hydroxynaphthalen-2-ylthio)acetic acid

HRID 1186675Notes

Reaction equation

HRID 1186675 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][CH2:22][C:23]([OH:25])=[O:24].[Cl:26]C1SC(S(/N=C2\C=C(Cl)C(=O)C3C\2=CC=CC=3)(=O)=O)=CC=1>>[Cl:26][C:18]1[S:17][C:16]([S:13]([NH:12][C:5]2[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[C:2]([OH:1])=[C:3]([S:21][CH2:22][C:23]([OH:25])=[O:24])[CH:4]=2)(=[O:15])=[O:14])=[CH:20][CH:19]=1

Participants

3

Reactant 2

HCID 15826052-{[1-Hydroxy-4-(thiophene-2-sulfonamido)naphthalen-2-yl]sulfanyl}acetic acidHCID 46909450(NE)-5-chloro-N-(3-chloro-4-oxonaphthalen-1-ylidene)thiophene-2-sulfonamide

Product 1

HCID 446093062-(4-(5-Chlorothiophene-2-sulfonamido)-1-hydroxynaphthalen-2-ylthio)acetic acid

Procedure

5.2.57 2-(4-(5-chlorothiophene-2-sulfonamido)-1-hydroxynaphthalen-2-ylthio)acetic acid (14o) was prepared according to the procedure of procedure B for 10a except using (E)-5-chloro-N-(3-chloro-4-oxonaphthalen-1(4H)-ylidene)thiophene-2-sulfonamide (12d), which afforded the title compound 32.4 mg (54%) as a white solid, m.p.: 143-145° C.

Sources & evidence

ORD record
ord-be331ffe9af34c19a4d47a8f764aab4a
Source dataset
uspto-grants-2014_03
Patent number
US08673910B2

Reaction notes

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