1-Iodopropane → HCID 23287659, compound

HRID 367121Notes

Reaction equation

[Br: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][CH3:24]>>[Br:1][C:2]1[CH:19]=[CH:18][C:5]([N:6]=[C:7]2[N:12]([CH2:22][CH2:23][CH3:24])[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 336431-Iodopropane

HCID 62714Lithium hydride

HCID 52306034H-Pyrido[3,2-e]-1,3-thiazin-4-one, 2-[(4-bromophenyl)amino]-

Product 1

HCID 23287659HCID 23287659, compoundYield 80.1%

Procedure

The reaction procedure of Example 11 was followed except that 900 mg (2.69 mmol) of 2-(4-bromoanilino)-4H-pyrido[3,2-e]-1,3-thiazin-4-one, 24 mg of lithium hydride and 503 mg of propyl iodide were used. The resulting residue was then purified through silica gel column chromatography (eluant: chloroform) to obtain 811 mg of 2-[(4-bromophenyl)imino]-2,3-dihydro-3-propyl-4H-pyrido[3,2-e]-1,3-thiazin-4-one (recrystallized from a mixture of ether and hexane) as a low polarity substance and 103 mg of 2-[N-(4-bromophenyl)-N-propylamino]-4H-pyrido[3,2-e]-1,3-thiazin-4-one (recrystallized from ether) as a high polarity substance.

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-50209093c1034576a095bc6cf586960a
Source dataset: uspto-grants-2000_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06133258

Reaction notes

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