P-Toluenesulfonamide → Ethyl 2-(1-oxo-4-(tosylimino)-1,4-dihydronaphthalen-2-ylthio)acetate

HRID 1186657Notes

Reaction equation

HRID 1186657 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].[CH3:28][C:29]1[CH:34]=[CH:33][C:32]([S:35]([NH2:38])(=[O:37])=[O:36])=[CH:31][CH:30]=1>C1COCC1.Cl[Ti](Cl)(Cl)Cl>[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](=[N:38][S:35]([C:32]2[CH:31]=[CH:30][C:29]([CH3:28])=[CH:34][CH:33]=2)(=[O:37])=[O:36])[CH:4]=[C:3]1[S:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24]

Participants

5

Reactant 2

HCID 6269P-ToluenesulfonamideHCID 58398202ethyl 2-[(4E)-1-oxo-4-thiophen-2-ylsulfonyliminonaphthalen-2-yl]sulfanylacetate

Product 1

HCID 67330702Ethyl 2-(1-oxo-4-(tosylimino)-1,4-dihydronaphthalen-2-ylthio)acetate

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

5.2.20 Ethyl 2-(1-oxo-4-(tosylimino)-1,4-dihydronaphthalen-2-ylthio)acetate (81) was prepared according to the procedure for 8a except using 4-methylbenzenesulfonamide, TiCl4.2THF and THF as solvent. The title compound 100.7 mg (46.9%) was obtained according to the workup procedure for 12a as a yellow solid, m.p.: ° C.

Sources & evidence

ORD record
ord-dce73b7faefe44f3a10eb082648840b4
Source dataset
uspto-grants-2014_03
Patent number
US08673910B2

Reaction notes

Loading…