1-Iodopropane → HCID 23287695, compound

HRID 367127Notes

Reaction equation

HRID 367127 reaction equation
[C:1]([C:3]1[CH:20]=[CH:19][C:6]([NH:7][C:8]2[S:9][C:10]3[N:18]=[CH:17][CH:16]=[CH:15][C:11]=3[C:12](=[O:14])[N:13]=2)=[CH:5][CH:4]=1)#[N:2].[H-].[Li+].[CH2:23](I)[CH2:24][CH3:25]>>[C:1]([C:3]1[CH:20]=[CH:19][C:6]([N:7]=[C:8]2[N:13]([CH2:23][CH2:24][CH3:25])[C:12](=[O:14])[C:11]3[CH:15]=[CH:16][CH:17]=[N:18][C:10]=3[S:9]2)=[CH:5][CH:4]=1)#[N:2]

Participants

4

Reactant 3

HCID 336431-IodopropaneHCID 62714Lithium hydrideHCID 23287603HCID 23287603, compound

Product 1

HCID 23287695HCID 23287695, compoundYield 70.9%

Procedure

The reaction procedure of Example 11 was followed except that 900 mg (3.21 mmol) of 2-(4-cyanoanilino)-4H-pyrido[3,2-e]-1,3-thiazin-4-one, 42 mg of lithium hydride and 655 mg of propyl iodide were used. The resulting residue was then purified through silica gel column chromatography (eluant: chloroform) to obtain 734 mg of 2-[(4-cyanophenyl)imino]-2,3-dihydro-3-propyl-4H-pyrido[3,2-e]-1,3-thiazin-4-one (71%, recrystallized from a mixture of ether and hexane) as a low polarity substance and 100 mg of 2-[N- (4-cyanophenyl)-N-propylamino]-4H-pyrido[3,2-e]-1,3-thiazin-4-one (10%, 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-2f38fc7969d2412e9f9114ee166dfaad
Source dataset
uspto-grants-2000_10
Patent number
US06133258

Reaction notes

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