Ethyl Acetate → Ethyl 2-(1-hydroxy-4-(4-nitrophenylsulfonamido)naphthalen-2-ylthio)acetate

HRID 1186660Notes

Reaction equation

HRID 1186660 reaction equation
[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)/[C:5](=N/S(C2SC=CC=2)(=O)=O)/[CH:4]=[C:3]1[S:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24].ClC1C(=O)C2C(=CC=CC=2)/C(=N/S(C2SC=CC=2)(=O)=O)/C=1.CCOC(C)=O.[N+:55]([C:58]1[CH:63]=[CH:62][C:61]([S:64]([NH2:67])(=[O:66])=[O:65])=[CH:60][CH:59]=1)([O-:57])=[O:56]>ClCCCl>[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([NH:67][S:64]([C:61]2[CH:60]=[CH:59][C:58]([N+:55]([O-:57])=[O:56])=[CH:63][CH:62]=2)(=[O:65])=[O:66])=[CH:4][C:3]=1[S:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 227844-NitrobenzenesulfonamideHCID 22524852(NE)-N-(3-chloro-4-oxonaphthalen-1-ylidene)thiophene-2-sulfonamideHCID 58398202ethyl 2-[(4E)-1-oxo-4-thiophen-2-ylsulfonyliminonaphthalen-2-yl]sulfanylacetate

Product 1

HCID 44608988Ethyl 2-(1-hydroxy-4-(4-nitrophenylsulfonamido)naphthalen-2-ylthio)acetate

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

5.2.25 Ethyl 2-(1-hydroxy-4-(4-nitrophenylsulfonamido)naphthalen-2-ylthio)acetate (9e) was prepared according to the procedure for 8a except using 4-nitrobenzenesulfonamide, 1,2-dichloroethane as solvent and applying 100° C. to the reaction. The reaction was worked up according to the procedure for 12a and the title compound was isolated from the product mixture by flash chromatography (EtOAc/Hex) affording 48 mg (10.4%) as a brown solid, m.p.: 143-145° C.

Workup

  1. customapplying 100° C. to the reaction

Sources & evidence

ORD record
ord-a91ed6187e374c20b899e1097c0613ab
Source dataset
uspto-grants-2014_03
Patent number
US08673910B2

Reaction notes

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