Pyridine → HCID 15592287, compound

HRID 1980674Notes

Reaction equation

HRID 1980674 reaction equation
[C:1]([N:10]([CH2:12][C:13]([NH2:15])=[S:14])[CH3:11])([O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[O:2].N1C=CC=CC=1.[Cl:22][CH2:23][C:24](=O)[CH2:25]Cl>C(O)C>[Cl:22][CH2:23][C:24]1[N:15]=[C:13]([CH2:12][N:10]([C:1]([O:3][C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)=[O:2])[CH3:11])[S:14][CH:25]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 107931,3-DichloroacetoneHCID 13102903HCID 13102903, compound

Product 1

HCID 15592287HCID 15592287, compoundYield 77.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a cooled solution of (N-carbophenoxy-N-methylamino)thioacetamide (1.0 g; 4.46 mmoles) and dry pyridine (0.36 ml, 4.46 mmoles) in 6 ml of absolute ethanol was added a solution of 1,3-dichloropropanone (0.57 g; 4.49 mmoles) in 3 ml of absolute ethanol. The mixture was heated at reflux temperature for 1.5 hours, then evaporated under reduced pressure and the oil residue partitioned between ether and water. The aqueous layer was extracted with ether and the combined ether phase was washed with water, saturated aqueous sodium chloride solution and dried. Filtration and evaporation yielded 1.02 g of the title compound as a viscous oil; TLC [silica/CH2Cl2 :CH3CN (85:15)]gave Rf =0.82. The NMR spectrum (60 MHz) in CDCl3 gave the following resonances δ7.16 (m, 6H); 4.77 (broad s, 2H); 4.60 (s, 2H); 3.07 (broad s, 3H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux temperature for 1.5 hours
  3. customevaporated under reduced pressure
  4. customthe oil residue partitioned between ether and water
  5. extractionThe aqueous layer was extracted with ether
  6. washthe combined ether phase was washed with water, saturated aqueous sodium chloride solution
  7. customdried
  8. filtrationFiltration and evaporation

Sources & evidence

ORD record
ord-98977d9d45174d4da4e768c208dfaab5
Source dataset
uspto-grants-1985_04
Patent number
US04510309

Reaction notes

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