Phosphorus oxychloride → HCID 21793934, compound

HRID 364243Notes

Reaction equation

HRID 364243 reaction equation
[CH3:1][S:2][C:3]1[N:8]=[C:7]([S:9][CH3:10])[CH:6]=[C:5]([CH2:11][NH:12][CH:13]=O)[N:4]=1.P(Cl)(Cl)(Cl)=O.O1CCOCC1.C(=O)(O)[O-].[Na+]>O>[CH3:1][S:2][C:3]1[N:4]2[CH:13]=[N:12][CH:11]=[C:5]2[CH:6]=[C:7]([S:9][CH3:10])[N:8]=1

Participants

6

Reactant 4

HCID 24813Phosphorus oxychlorideHCID 312751,4-DioxaneHCID 516892Sodium BicarbonateHCID 21793931HCID 21793931, compound

Product 1

HCID 21793934HCID 21793934, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

A mixture of 3.00 g (13.1 mmole) of 2,4-bis(methylthio)-6-formylaminomethylpyrimidine, 2.25 g (14.2 mmole) of phosphorous oxychloride and 50 ml of dioxane was stirred at 20° C. for 20 hours, then heated at reflux for 0.5 hour. The mixture was poured into 100 ml of water, neutralized with solid sodium bicarbonate and extracted with chloroform. The chloroform extracts were combined, washed with water and dried over magnesium sulfate. Evaporation of the solvent provided a light yellow solid, 5,7-bis(methylthio)imidazo[1,5-c]pyrimidine. The structural assignment was confirmed by infrared and nuclear magnetic resonance spectral analyses.

Workup

  1. temperatureheated
  2. temperatureat reflux for 0.5 hour
  3. extractionextracted with chloroform
  4. washwashed with water
  5. dry with materialdried over magnesium sulfate
  6. customEvaporation of the solvent

Sources & evidence

ORD record
ord-af650e9c3843403d87e9b7c5b1502de5
Source dataset
uspto-grants-1986_08
Patent number
US04604466

Reaction notes

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