Ethyl Thioglycolate → Methyl-3-(4-(4,5-dichlorothiophene-2-sulfonamido)-1-hydroxynaphthalen-2-ylthio)propanoate

HRID 1186673Notes

Reaction equation

HRID 1186673 reaction equation
OC1C2C(=CC=CC=2)C(N[S:13]([C:16]2SC=CC=2)(=O)=O)=CC=1SCC(O)=O.[Cl:26][C:27]1[CH:28]=[C:29]([S:33]([N:36]=[C:37]2[C:46]3[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=3)[C:40](=[O:47])[C:39](Cl)=[CH:38]2)(=[O:35])=[O:34])[S:30][C:31]=1[Cl:32].S[CH2:50][C:51]([O:53][CH2:54]C)=[O:52]>CCOC(C)=O>[CH3:54][O:53][C:51](=[O:52])[CH2:50][CH2:16][S:13][C:39]1[CH:38]=[C:37]([NH:36][S:33]([C:29]2[S:30][C:31]([Cl:32])=[C:27]([Cl:26])[CH:28]=2)(=[O:35])=[O:34])[C:46]2[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=2)[C:40]=1[OH:47]

Participants

5

Reactant 3

HCID 12185Ethyl ThioglycolateHCID 15826052-{[1-Hydroxy-4-(thiophene-2-sulfonamido)naphthalen-2-yl]sulfanyl}acetic acidHCID 673306684,5-dichloro-N-(3-chloro-4-oxonaphthalen-1(4H)-ylidene)thiophene-2-sulfonamide

Product 1

HCID 44609146Methyl-3-(4-(4,5-dichlorothiophene-2-sulfonamido)-1-hydroxynaphthalen-2-ylthio)propanoate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

5.2.55 Methyl-3-(4-(4,5-dichlorothiophene-2-sulfonamido)-1-hydroxynaphthalen-2-ylthio)propanoate (14m) was prepared according to the procedure of procedure B for 10a except using 4,5-dichloro-N-(3-chloro-4-oxonaphthalen-1(4H)-ylidene)thiophenesulfonamide (12c) and ethyl mercaptoacetate, which afforded the title compound 16.1 mg (33%) as a grey solid after flash chromatography (Hex/EtOAc), m.p.: ° C.

Sources & evidence

ORD record
ord-651188344f86498fbe2ddc5811099be4
Source dataset
uspto-grants-2014_03
Patent number
US08673910B2

Reaction notes

Loading…