Phosphorus oxychloride → HCID 20381964, compound

HRID 1448125Notes

Reaction equation

HRID 1448125 reaction equation
[Cl:1][CH2:2][CH2:3][N:4]1[CH:13]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([Cl:20])[CH:11]=2)[NH:6][C:5]1=O.P(Cl)(Cl)([Cl:24])=O>>[Cl:24][C:5]1[N:4]([CH2:3][CH2:2][Cl:1])[CH:13]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([Cl:20])[CH:11]=2)[N:6]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 20278944HCID 20278944, compound

Product 1

HCID 20381964HCID 20381964, compound

Conditions

Temperature
105 °C

Procedure

A mixture of 3.21 g of 3-(2-chloroethyl)-4-phenyl-6-chloro-3,4-dihydro-2(1H)-quinazolinone and 10 g of phosphorus oxychloride was heated with stirring at 105° C. for 20 hours. The resulting solution was evaporated in vacuo to dryness and the resulting residue was dissolved in chloroform. The chloroform solution was washed with an aqueous sodium bicarbonate solution and then with water, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure to give 2,6-dichloro-3-(2-chloroethyl)-4-phenyl-3,4-dihydroquinazoline. The crude solid was chromatographed on silica gel using chloroform as an eluting solvent. Removal of the solvent and recrystallization of the residue from a mixture of benzene and petroleum benzin gave 0.60 g of pure product, m.p. 169°-170° C. To a solution of 0.34 g of 2,6-dichloro-3-(2-chloroethyl)-4-phenyl-3,4-dihydroquinazoline in 2 ml of dimethylformamide was added 0.59 g of n-propylamine and the mixture was heated at 105° C. for 5 hours. After cooling, 10 ml of water was added to the reaction mixture and the resulting mixture was extracted with chloroform. The organic phase was separated, washed with water and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure and the residue was chromatographed on silica gel using chloroform as an eluting solvent to give 0.24 g of 1-(n-propyl)-5-phenyl-7-chloro-1,2,3,5-tetrahydroimidazo-[2,1-b]quinazoline hydrochloride. Recrystallization from a mixture of ethanol and diisopropyl ether gave slightly brown fine crystals, m.p. 258° C.

Workup

  1. temperaturewas heated
  2. customThe resulting solution was evaporated in vacuo to dryness
  3. dissolutionthe resulting residue was dissolved in chloroform
  4. washThe chloroform solution was washed with an aqueous sodium bicarbonate solution
  5. dry with materialwith water, and dried over anhydrous sodium sulfate
  6. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-16ec4e02032648e7b51b5d7693a70379
Source dataset
uspto-grants-1979_12
Patent number
US04179560

Reaction notes

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