Naphthalene-2-sulfonamide → N-(3-chloro-4-oxonaphthalen-1(4H)-ylidene)naphthalene-2-sulfonamide

HRID 1186664Notes

Reaction equation

HRID 1186664 reaction equation
[Cl:1][C:2]1[C:11](=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)/[C:4](=N/S(C2SC=CC=2)(=O)=O)/[CH:3]=1.[CH:22]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:25]=[CH:24][C:23]=1[S:32]([NH2:35])(=[O:34])=[O:33]>C1COCC1.Cl[Ti](Cl)(Cl)Cl>[Cl:1][C:2]1[C:11](=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[N:35][S:32]([C:23]2[CH:24]=[CH:25][C:26]3[C:31](=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH:22]=2)(=[O:34])=[O:33])[CH:3]=1

Participants

5

Reactant 2

HCID 232997Naphthalene-2-sulfonamideHCID 22524852(NE)-N-(3-chloro-4-oxonaphthalen-1-ylidene)thiophene-2-sulfonamide

Product 1

HCID 7559435N-(3-chloro-4-oxonaphthalen-1(4H)-ylidene)naphthalene-2-sulfonamide

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

5.2.35 N-(3-chloro-4-oxonaphthalen-1(4H)-ylidene)naphthalene-2-sulfonamide (12f) was prepared according to the procedure for (12a) except using naphthalene-2-sulfonamide, TiCl4.2THF and THF as solvent which afforded the title compound 594.8 mg (77.9%) as a yellow solid, m.p.: 200-202° C.

Sources & evidence

ORD record
ord-a695296c102c4f5da18e355a81cf218c
Source dataset
uspto-grants-2014_03
Patent number
US08673910B2

Reaction notes

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