Chloroacetone → HCID 23287674, compound

HRID 367215Notes

Reaction equation

HRID 367215 reaction equation
[H-].[Li+].[Cl:3][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.Cl[CH2:23][C:24](=[O:26])[CH3:25]>CN(C=O)C>[Cl:3][C:4]1[CH:21]=[CH:20][C:7]([N:8]=[C:9]2[N:14]([CH2:23][C:24](=[O:26])[CH3:25])[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

Participants

5

Reactant 3

HCID 6571ChloroacetoneHCID 62714Lithium hydrideHCID 42920704H-Pyrido[3,2-e]-1,3-thiazin-4-one, 2-[(4-chlorophenyl)amino]-2×

Product 1

HCID 23287674HCID 23287674, compoundYield 50.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

In an atmosphere of argon, a mixture of 26 mg (3.3 mmol) of lithium hydride and 5 ml of DMF was put in a 100 ml flask. To the flask was then connected a dropping funnel which contained 800 mg (2.8 mmol) of 2-(4-chloroanilino)-4H-pyrido[3,2-e]-1,3-thiazin-4-one and 10 ml of DMF. The solution of 2-(4-chloroanilino)-4H-pyrido[3,2-e]-1,3-thiazin-4-one was then added dropwise to the aforementioned mixture with stirring in 3 minutes. The mixture was further stirred for 30 minutes. To the mixture was then added a mixture of 332 mg of chloroacetone and 2 ml of DMF. The mixture was then stirred for 8 hours. After the termination of reaction, the mixture was concentrated under reduced pressure. The resulting residue was then extracted with water and ethyl acetate. The resulting organic phase was separated, washed with water and saturated brine, and then dried over sodium sulfate. The drying agent was then removed by filtration. The filtrate was then concentrated under reduced pressure. The resulting residue was then purified through silica gel column chromatography (eluant: 1/1 mixture of ethyl acetate and normal hexane). As a result, 487 mg of 2-[(4-chlorophenyl)imino]-2,3-dihydro-3-(2-oxopropyl)-4H-pyrido[3,2-e]-1,3-thiazin-4-one was obtained as a low polarity substance, and 267 mg of 2-[N-(4-chlorophenyl)-N-(2-oxopropyl)amino]-4H-pyrido[3,2-e]-1,3-thiazin-4-one was obtained as a high polarity substance. 1) 2-[(4-Chlorophenyl)imino]-2,3-dihydro-3-(2-oxopropyl)-4H-pyrido[3,2-e]-1,3-thiazin-4-one

Workup

  1. customwas put in a 100 ml flask
  2. stirringThe mixture was further stirred for 30 minutes
  3. additionTo the mixture was then added
  4. stirringThe mixture was then stirred for 8 hours
  5. customAfter the termination of reaction
  6. concentrationthe mixture was concentrated under reduced pressure
  7. extractionThe resulting residue was then extracted with water and ethyl acetate
  8. customThe resulting organic phase was separated
  9. washwashed with water and saturated brine
  10. dry with materialdried over sodium sulfate
  11. customThe drying agent was then removed by filtration
  12. concentrationThe filtrate was then concentrated under reduced pressure
  13. customThe resulting residue was then purified through silica gel column chromatography (eluant: 1/1 mixture of ethyl acetate and normal hexane)

Sources & evidence

ORD record
ord-675badf9fd7a4fd1bca809005627c2e7
Source dataset
uspto-grants-2000_10
Patent number
US06133258

Reaction notes

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