Methyl iodide → HCID 23287672, compound

HRID 367140Notes

Reaction equation

[N+:1]([C:4]1[CH:21]=[CH:20][C:7]([NH:8][C:9]2[S:10][C:11]3[N:19]=[CH:18][CH:17]=[CH:16][C:12]=3[C:13](=[O:15])[N:14]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[H-].[Li+].[CH3:24]I>>[CH3:24][N:14]1[C:13](=[O:15])[C:12]2[CH:16]=[CH:17][CH:18]=[N:19][C:11]=2[S:10][C:9]1=[N:8][C:7]1[CH:20]=[CH:21][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1

Participants

Reactant 3

HCID 6328Methyl iodide

HCID 62714Lithium hydride

HCID 4917182ST4104869

Product 1

HCID 23287672HCID 23287672, compoundYield 80.2%

Procedure

The reaction procedure of Example 11 was followed except that 901 mg (3.0 mmol) of 2-(4-nitroanilino)-4H-pyrido[3,2-e]-1,3-thiazin-4-one, 30 mg of lithium hydride and 511 mg of methyl iodide were used. The resulting residue was then purified through silica gel chromatography (eluant: chloroform) to obtain 756 mg of 2,3-dihydro-3-methyl-2-[(4-nitrophenyl)imino]-4H-pyrido[3,2-e]-1,3-thiazin-4-one (80%, recrystallized from a mixture of ether and ethanol).

Workup

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

Sources & evidence

ORD record: ord-39092e7b31c6454689fcc63f419af80b
Source dataset: uspto-grants-2000_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06133258

Reaction notes

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