1-Iodopropane → 2,3-dihydro-2-[(4-methylphenyl)imino)-3-propyl-4H-pyrido[3,2-e]-1,3-thiazin-4-one

HRID 367116

Reaction equation

HRID 367116 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][CH3:24]>CN(C=O)C>[CH3:1][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

5

Reactant 3

HCID 336431-IodopropaneHCID 62714Lithium hydrideHCID 973891Bas 09531330

Product 1

HCID 154855002,3-dihydro-2-[(4-methylphenyl)imino)-3-propyl-4H-pyrido[3,2-e]-1,3-thiazin-4-oneYield 56.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 900 mg (3.34 mmol) of 2-(4-methylanilino)-4H-pyrido[3,2-e]-1,3-thiazin-4-one and 15 ml of DMF was added 27 mg of lithium hydride in a stream of argon, and it was stirred for 30 minutes at room temperature. To the mixture was then added 568 mg of n-propyl iodide. The mixture was then stirred for 2 hours. After the termination of the reaction, the mixture was concentrated under reduced pressure. To the resulting residue was added water and ethyl acetate, and extracted. The resulting organic phase was separated, washed with water and saturated brine, dried over sodium sulfate, and then concentrated under reduced pressure. The resulting residue was then purified through silica gel column chromatography (eluant: chloroform) to obtain 584 mg of 2,3-dihydro-2-[(4-methylphenyl)imino)-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 179 mg of 2-[N-(4-methylphenyl)-N-propylamino]-4H-pyrido[3,2-e]-1,3-thiazin-4-one (recrystallized from ether) as a high polarity substance.

Workup

  1. stirringThe mixture was then stirred for 2 hours
  2. customAfter the termination of the reaction
  3. concentrationthe mixture was concentrated under reduced pressure
  4. additionTo the resulting residue was added water and ethyl acetate
  5. extractionextracted
  6. customThe resulting organic phase was separated
  7. washwashed with water and saturated brine
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe resulting residue was then purified through silica gel column chromatography (eluant: chloroform)

Sources & evidence

ORD record
ord-8b6ed8c66f4046e990aa25c01f2b6cbf
Source dataset
uspto-grants-2000_10
Patent number
US06133258

Linked notes

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