Chloroacetone → HCID 14423125, compound

HRID 476570Notes

Reaction equation

HRID 476570 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[N:10]([CH2:11][C:12]([N:14]3[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]3)=[O:13])[C:9](=[O:20])[S:8][C:5]2=[N:6][CH:7]=1.Cl[CH2:22][C:23](=[O:25])[CH3:24].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]2[N:10]([CH2:11][C:12]([N:14]3[CH2:15][CH2:16][N:17]([CH2:22][C:23]([CH3:24])=[O:25])[CH2:18][CH2:19]3)=[O:13])[C:9](=[O:20])[S:8][C:5]2=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 6571ChloroacetoneHCID 11430Potassium CarbonateHCID 19837972HCID 19837972, compound

Product 1

HCID 14423125HCID 14423125, compoundYield 47.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 6-chloro-2-oxo-1-(1-piperazinyl)carbonylmethyl-1,2-dihydrothiazolo[5,4-b]pyridine (0.80 g), chloroacetone (0.24 g), and potassium carbonate (0.35 g) in dry N,N-dimethylformamide (2.4 ml) was heated at 80° C. for 30 min. The mixture was poured into an ice-water, and the precipitates obtained were extracted with chloroform. The chloroform layer was washed with water, dried over magnesium sulfate, and evaporated to give crude crystals (0.85 g). The crude crystals were recrystallized from a mixture of chloroform and ethyl acetate to give 6-chloro-2-oxo-1-[(4-acetonyl-1-piperazinyl)carbonylmethyl]-1,2-dihydrothiazolo[5,4-b]pyridine (0.45 g).

Workup

  1. customthe precipitates obtained
  2. extractionwere extracted with chloroform
  3. washThe chloroform layer was washed with water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customto give crude crystals (0.85 g)
  7. customThe crude crystals were recrystallized from a mixture of chloroform and ethyl acetate

Sources & evidence

ORD record
ord-910b1374cf584bb4ab1ed2538daba317
Source dataset
uspto-grants-1989_12
Patent number
US04885297

Reaction notes

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