Iodoethane → 2-[(4-chlorophenyl)imino]-2,3-dihydro-3-ethyl-4H-pyrido[3,2-e]-1,3-thiazin-4-one

Reaction equation

[Cl:1][C:2]1[CH:19]=[CH:18][C:5]([NH:6][C:7]2[S:8][C:9]3[N:17]=[CH:16][CH:15]=[CH:14][C:10]=3[C:11](=[O:13])[N:12]=2)=[CH:4][CH:3]=1.[H-].[Li+].[CH2:22](I)[CH3:23]>>[Cl:1][C:2]1[CH:19]=[CH:18][C:5]([N:6]=[C:7]2[N:12]([CH2:22][CH3:23])[C:11](=[O:13])[C:10]3[CH:14]=[CH:15][CH:16]=[N:17][C:9]=3[S:8]2)=[CH:4][CH:3]=1

Participants

Reactant 3

HCID 6340Iodoethane

HCID 62714Lithium hydride

HCID 42920704H-Pyrido[3,2-e]-1,3-thiazin-4-one, 2-[(4-chlorophenyl)amino]-

Product 1

HCID 232875682-[(4-chlorophenyl)imino]-2,3-dihydro-3-ethyl-4H-pyrido[3,2-e]-1,3-thiazin-4-oneYield 58.4%

Procedure

The reaction procedure of Example 11 was followed except that 900 mg (3.11 mmol) of 2-(4-chloroanilino)-4H-pyrido[3,2-e]-1,3-thiazin-4-one, 25 mg of lithium hydride and 584 mg of ethyl iodide were used. The resulting residue was then purified through silica gel column chromatography (eluant: chloroform) to obtain 577 mg of 2-[(4-chlorophenyl)imino]-2,3-dihydro-3-ethyl-4H-pyrido[3,2-e]-1,3-thiazin-4-one (58%, recrystallized from a mixture of ether and hexane) as a low polarity substance and 61 mg of 2-[N-(4-chlorophenyl)-N-ethylamino]-4H-pyrido[3,2-e]-1,3-thiazin-4-one (6%, recrystallized from ether) as a high polarity substance.