Butyl iodide → 3-butyl-2,3-dihydro-2-[(4-methylphenyl)imino]-4H-pyrido[3,2-e]-1,3-thiazin-4-one

HRID 367117

Reaction equation

HRID 367117 reaction equation
[CH3:1][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)[CH2:23][CH2:24][CH3:25]>>[CH2:22]([N:12]1[C:11](=[O:13])[C:10]2[CH:14]=[CH:15][CH:16]=[N:17][C:9]=2[S:8][C:7]1=[N:6][C:5]1[CH:18]=[CH:19][C:2]([CH3:1])=[CH:3][CH:4]=1)[CH2:23][CH2:24][CH3:25]

Participants

4

Reactant 3

HCID 10962Butyl iodideHCID 62714Lithium hydrideHCID 973891Bas 09531330

Product 1

HCID 232877283-butyl-2,3-dihydro-2-[(4-methylphenyl)imino]-4H-pyrido[3,2-e]-1,3-thiazin-4-oneYield 52%

Procedure

The reaction procedure of Example 11 was followed except that 909 mg (3.38 mmol) of 2-(4-methylanilino)-4H-pyrido[3,2-e]-1,3-thiazin-4-one, 27 mg of lithium hydride and 621 mg of butyl iodide were used. The resulting residue was then purified through silica gel column chromatography (eluant: chloroform) to obtain 571 mg of 3-butyl-2,3-dihydro-2-[(4-methylphenyl)imino]-4H-pyrido[3,2-e]-1,3-thiazin-4-one (52%, recrystallized from a mixture of ether and hexane) as a low polarity substance and 157 mg of 2-[N-butyl-N-(4-methylphenyl)amino]-4H-pyrido[3,2-e]-1,3-thiazin-4-one (recrystallized from ether) as a high polarity substance.

Workup

  1. customThe reaction procedure of Example 11
  2. customThe resulting residue was then purified through silica gel column chromatography (eluant: chloroform)

Sources & evidence

ORD record
ord-1bb984186b35453f9956c17d621f039f
Source dataset
uspto-grants-2000_10
Patent number
US06133258

Linked notes

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