Ethyl Thioglycolate → Ethyl 2-(4-(biphenyl-4-ylsulfonamido)-1-hydroxynaphthalen-2-ylthio)acetate

HRID 1186678Notes

Reaction equation

HRID 1186678 reaction equation
OC1C2C(=CC=CC=2)C(NS(C2SC=CC=2)(=O)=O)=CC=1SCC(O)=O.Cl[C:27]1[C:36](=[O:37])[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)/[C:29](=[N:38]/[S:39]([C:42]2[CH:47]=[CH:46][C:45]([C:48]3[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=3)=[CH:44][CH:43]=2)(=[O:41])=[O:40])/[CH:28]=1.[SH:54][CH2:55][C:56]([O:58][CH2:59][CH3:60])=[O:57]>>[C:45]1([C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)[CH:46]=[CH:47][C:42]([S:39]([NH:38][C:29]2[C:30]3[C:35](=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:36]([OH:37])=[C:27]([S:54][CH2:55][C:56]([O:58][CH2:59][CH3:60])=[O:57])[CH:28]=2)(=[O:41])=[O:40])=[CH:43][CH:44]=1

Participants

4

Reactant 3

HCID 12185Ethyl ThioglycolateHCID 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 46908188Ethyl 2-(4-(biphenyl-4-ylsulfonamido)-1-hydroxynaphthalen-2-ylthio)acetate

Procedure

5.2.60 Ethyl 2-(4-(biphenyl-4-ylsulfonamido)-1-hydroxynaphthalen-2-ylthio)acetate (14r) was prepared according to the procedure of procedure B for 10a except using (E)-N-(3-chloro-4-oxonaphthalen-1(4H)-ylidene)biphenyl-4-sulfonamide (12b) and ethyl mercapto-acetate, which afforded the title compound 71.5 mg (85.5%) as an off-white solid, m.p.: 166-168° C.

Sources & evidence

ORD record
ord-bd01724a34da4290abd69cf478810e87
Source dataset
uspto-grants-2014_03
Patent number
US08673910B2

Reaction notes

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