Dimethylformamide → HCID 15337420, compound

HRID 260525Notes

Reaction equation

HRID 260525 reaction equation
O[C:2]1[N:3]=[C:4]2[S:11][CH2:10][CH2:9][N:5]2[C:6](=[O:8])[CH:7]=1.CN(C)[CH:14]=[O:15].P(Cl)(Cl)([Cl:19])=O>>[Cl:19][C:2]1[N:3]=[C:4]2[S:11][CH2:10][CH2:9][N:5]2[C:6](=[O:8])[C:7]=1[CH:14]=[O:15]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 135408037HCID 135408037, compound

Product 1

HCID 15337420HCID 15337420, compoundYield 69%

Procedure

In 40 ml of phosphorus oxychloride was dissolved 10.0 g (58.8 mmol) of 2,3-dihydro-7-hydroxy-5-oxo-5H-thiazolo[3,2-a]pyrimidine [J. Am. Chem. Soc., 64, 2709 (1942)], and 6.0 ml of dimethylformamide was added dropwise to the solution with stirring under ice-cooling. Then, the reaction mixture was heated under reflux for 30 minutes. After concentration of the reaction mixture to dryness under reduced pressure, the oily residue was poured by portions into ice water. The precipitated crystals were collected by filtration, and recrystallized from chloroform to give 8.8 g (69%) of the desired compound as pale yellow crystals.

Workup

  1. additionwas added dropwise to the solution
  2. temperaturecooling
  3. temperatureThen, the reaction mixture was heated
  4. temperatureunder reflux for 30 minutes
  5. filtrationThe precipitated crystals were collected by filtration
  6. customrecrystallized from chloroform

Sources & evidence

ORD record
ord-dbbf6704c515458d9d85ca31fcfb00ae
Source dataset
uspto-grants-1996_06
Patent number
US05527908

Reaction notes

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