Triethylamine → HCID 10933458, compound

HRID 1598537Notes

Reaction equation

HRID 1598537 reaction equation
[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=O)[NH:3][C:2]1=O.[CH2:13]([N:15](CC)[CH2:16][CH3:17])[CH3:14].P(Cl)(Cl)([Cl:22])=O>>[Cl:22][C:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[N:1]=[C:2]([N:15]([CH2:16][CH3:17])[CH2:13][CH3:14])[N:3]=1

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 24813Phosphorus oxychlorideHCID 64048Quinazolinedione

Product 1

HCID 10933458HCID 10933458, compound

Procedure

20.0 g of 1H,3H-quinazoline-2,4-dione were dissolved in 280 ml of phosphorus oxychloride, and 60 ml of triethylamine were added. After refluxing for 75 minutes, the excess phosphorus oxychloride was distilled off under vacuum and the residue was slowly introduced into 200 ml of ice-cold 1N sodium hydroxide solution. Extraction with dichloromethane (three times 150 ml), washing of the organic phase with water (three times 100 ml), drying over magnesium sulfate and distillation of the solvent on a rotary evaporator gave a brown oil, which could be used in the next reaction without further purification. Yield: 17.7 g (60%)

Workup

  1. temperatureAfter refluxing for 75 minutes
  2. distillationthe excess phosphorus oxychloride was distilled off under vacuum
  3. additionthe residue was slowly introduced into 200 ml of ice-cold 1N sodium hydroxide solution
  4. extractionExtraction with dichloromethane (three times 150 ml)
  5. washwashing of the organic phase with water (three times 100 ml)
  6. dry with materialdrying over magnesium sulfate and distillation of the solvent on a rotary evaporator
  7. customgave a brown oil, which
  8. customcould be used in the next reaction without further purification

Sources & evidence

ORD record
ord-6c687394c8c04619a5ac7a3d3c3659b1
Source dataset
uspto-grants-1998_04
Patent number
US05739127

Reaction notes

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