2-Mercaptobenzoic Acid → 2-(4-(Biphenyl-4-ylsulfonamido)-1-hydroxynaphthalen-2-ylthio)benzoic acid

HRID 1186680Notes

Reaction equation

HRID 1186680 reaction equation
OC1C2C(=CC=CC=2)C(NS(C2SC=CC=2)(=O)=O)=CC=1SCC(O)=O.[CH:26]1[CH:31]=[C:30]([C:32]([OH:34])=[O:33])[C:29]([SH:35])=[CH:28][CH:27]=1.Cl[C:37]1[C:46](=[O:47])[C:45]2[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=2)/[C:39](=[N:48]/[S:49]([C:52]2[CH:57]=[CH:56][C:55]([C:58]3[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=3)=[CH:54][CH:53]=2)(=[O:51])=[O:50])/[CH:38]=1>>[C:55]1([C:58]2[CH:59]=[CH:60][CH:61]=[CH:62][CH:63]=2)[CH:56]=[CH:57][C:52]([S:49]([NH:48][C:39]2[C:40]3[C:45](=[CH:44][CH:43]=[CH:42][CH:41]=3)[C:46]([OH:47])=[C:37]([S:35][C:29]3[CH:28]=[CH:27][CH:26]=[CH:31][C:30]=3[C:32]([OH:34])=[O:33])[CH:38]=2)(=[O:51])=[O:50])=[CH:53][CH:54]=1

Participants

4

Reactant 3

HCID 54432-Mercaptobenzoic AcidHCID 15826052-{[1-Hydroxy-4-(thiophene-2-sulfonamido)naphthalen-2-yl]sulfanyl}acetic acidHCID 58398230(NE)-N-(3-chloro-4-oxonaphthalen-1-ylidene)-4-phenylbenzenesulfonamide

Product 1

HCID 446093082-(4-(Biphenyl-4-ylsulfonamido)-1-hydroxynaphthalen-2-ylthio)benzoic acid

Procedure

5.2.62 2-(4-(biphenyl-4-ylsulfonamido)-1-hydroxynaphthalen-2-ylthio)benzoic acid (14t) was prepared according to the procedure of procedure B for 10a except using 2-thiosalicylic acid and (E)-N-(3-chloro-4-oxonaphthalen-1(4H)-ylidene)biphenyl-4-sulfonamide (12b), which afforded the title compound 17.4 mg (65.9%) as an off-white solid, m.p.: 205° C. (dec.).

Sources & evidence

ORD record
ord-44a9883ad1c544baa052de2937dc4d7f
Source dataset
uspto-grants-2014_03
Patent number
US08673910B2

Reaction notes

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