(4-Chlorophenyl)methanesulfonamide → Ethyl 2-(4-(4-chlorobenzylsulfonylimino)-1-oxo-1,4-dihydronaphthalen-2-ylthio)-acetate

HRID 1186658Notes

Reaction equation

HRID 1186658 reaction equation
[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)/[C:5](=[N: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]([O:25][CH2:26][CH3:27])=[O:24].[Cl:28][C:29]1C=CC(CS(N)(=O)=O)=[CH:31][CH:30]=1>C1COCC1.Cl[Ti](Cl)(Cl)Cl>[Cl:28][C:29]1[CH:18]=[CH:19][C:20]([CH2:16][S:13]([N:12]=[C:5]2[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[C:2](=[O:1])[C:3]([S:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:4]2)(=[O:14])=[O:15])=[CH:31][CH:30]=1

Participants

5

Reactant 2

HCID 581056(4-Chlorophenyl)methanesulfonamideHCID 58398202ethyl 2-[(4E)-1-oxo-4-thiophen-2-ylsulfonyliminonaphthalen-2-yl]sulfanylacetate

Product 1

HCID 67330733Ethyl 2-(4-(4-chlorobenzylsulfonylimino)-1-oxo-1,4-dihydronaphthalen-2-ylthio)-acetate

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

5.2.21 Ethyl 2-(4-(4-chlorobenzylsulfonylimino)-1-oxo-1,4-dihydronaphthalen-2-ylthio)-acetate (8g) was prepared according to the procedure for 8a except using (4-chlorophenyl)methanesulfonamide, TiCl4.2THF and THF as solvent. The title compound 130 mg (56%) was obtained according to the workup procedure for 12a as a yellow solid, m.p.: ° C.

Sources & evidence

ORD record
ord-a745b0517eb144c3ba1430bf7173ae41
Source dataset
uspto-grants-2014_03
Patent number
US08673910B2

Reaction notes

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