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

HRID 1186677Notes

Reaction equation

HRID 1186677 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]2S[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[C:27]1[C:36](=O)[C:35]2[C:30](=CC=CC=2)/[C:29](=N/S(C2C=CC3C(=CC=CC=3)C=2)(=O)=O)/[CH:28]=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[CH:20]=[CH:19][C:18]3[C:36](=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH:35]=2)(=[O:14])=[O:15])=[CH:4][C:3]=1[S:21][CH2:22][C:23]([OH:25])=[O:24]

Participants

3

Reactant 2

HCID 15826052-{[1-Hydroxy-4-(thiophene-2-sulfonamido)naphthalen-2-yl]sulfanyl}acetic acidHCID 24282891(NE)-N-(3-chloro-4-oxonaphthalen-1-ylidene)naphthalene-2-sulfonamide

Product 1

HCID 1184140({1-Hydroxy-4-[(2-naphthylsulfonyl)amino]-2-naphthyl}sulfanyl)acetic acid

Procedure

5.2.59 2-(1-hydroxy-4-(naphthalene-2-sulfonamido)naphthalen-2-ylthio)acetic acid (14q) was prepared according to the procedure of procedure B for 10a except using (E)-N-(3-chloro-4-oxonaphthalen-1(4H)-ylidene)naphthalene-2-sulfonamide (12f), which afforded the title compound 64.3 mg (73.5%) as a white solid, m.p.: 185-187° C.

Sources & evidence

ORD record
ord-273947029fb047e98e6ec795f8900e21
Source dataset
uspto-grants-2014_03
Patent number
US08673910B2

Reaction notes

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