1-Iodopropane → HCID 23287648, compound

HRID 367141Notes

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+].[CH2:24](I)[CH2:25][CH3:26]>>[N+:1]([C:4]1[CH:21]=[CH:20][C:7]([N:8]=[C:9]2[N:14]([CH2:24][CH2:25][CH3:26])[C:13](=[O:15])[C:12]3[CH:16]=[CH:17][CH:18]=[N:19][C:11]=3[S:10]2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

Reactant 3

HCID 336431-Iodopropane

HCID 62714Lithium hydride

HCID 4917182ST4104869

Product 1

HCID 23287648HCID 23287648, compoundYield 58.7%

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 612 mg of propyl iodide were used. The resulting residue was then purified through silica gel column chromatography (eluant: chloroform) to obtain 603 mg of 2,3-dihydro-2-[(4-nitrophenyl)imino]-3-propyl-4H-pyrido[3,2-e]-1,3-thiazin-4-one (59%, recrystallized from a mixture of ether and ethanol).

Workup

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

Sources & evidence

ORD record: ord-e2d94e37d9994102ba19cc5fea565543
Source dataset: uspto-grants-2000_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06133258

Reaction notes

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