Diethylene Glycol Monoethyl Ether → Proquazone

HRID 426829Notes

Reaction equation

HRID 426829 reaction equation
[CH3:1][CH:2]1[CH2:11][C:10]2[N:9]([CH:12]([CH3:14])[CH3:13])[C:8](=[O:15])[N:7]=[C:6]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:5]=2[CH2:4][CH2:3]1.[S].[OH-].[Na+].[Cl-].[Ca+2].[Cl-].CCOCCOCCO>C1C=CC=CC=1.Cl>[CH:12]([N:9]1[C:10]2[C:5](=[CH:4][CH:3]=[C:2]([CH3:1])[CH:11]=2)[C:6]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[N:7][C:8]1=[O:15])([CH3:14])[CH3:13]

Participants

8

Reactant 5

HCID 8146Diethylene Glycol Monoethyl EtherHCID 14798Sodium HydroxideHCID 5284359Calcium ChlorideHCID 5362487SulfurHCID 20390097HCID 20390097, compound

Product 1

HCID 31508Proquazone

Reagents, catalysts & solvents 2

HCID 241BenzeneSolvent2×HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of 28.2 g. of 7-methyl-1-isopropyl-4-phenyl-5,6,7,8-tetrahydro-2(1H) quinazolinone, 9.6 g. of sulfur, 10 gms of sodium hydroxide, 20 gms of calcium chloride and 200 mls of carbitol (2-[2-ethoxyethoxy]ethanol) is heated under a nitrogen blanket at 150° C. for 2 hours. The resulting mixture is then cooled to 65° C., 500 mls. of benzene added and the mixture cooled with stirring to 15° C. and the liquid phase decanted. The organic phase is washed with water and evaporated to obtain an oil which is dissolved in a mixture of 100 mls of benzene and 100 mls of 50% aqueous hydrochloric acid. The resulting mixture is stirred for one hour at room temperature, the phases separated and the acid phase treated with 50 mls of benzene. The acid phase is neutralized with 50% sodium hydroxide solution, extracted with 150 mls of benzene and the benzene extracts washed with water until neutral. After drying over sodium sulfate, the benzene solution is evaporated to obtain the crude product which is recrystallized from ethylacetate to obtain 1-isopropyl-4-phenyl-7-methyl-2[1H]quinazolinone, m.p. 141°-142° C.

Workup

  1. additionA mixture of 28.2 g
  2. temperaturethe mixture cooled
  3. customthe liquid phase decanted
  4. washThe organic phase is washed with water
  5. customevaporated
  6. customto obtain an oil which
  7. stirringThe resulting mixture is stirred for one hour at room temperature
  8. customthe phases separated
  9. additionthe acid phase treated with 50 mls of benzene
  10. extractionextracted with 150 mls of benzene
  11. washthe benzene extracts washed with water until neutral
  12. dry with materialAfter drying over sodium sulfate
  13. customthe benzene solution is evaporated
  14. customto obtain the crude product which
  15. customis recrystallized from ethylacetate

Sources & evidence

ORD record
ord-68094627a2b64fcca68513193b826402
Source dataset
uspto-grants-1979_10
Patent number
US04171441

Reaction notes

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