Ammonia → 4-Chloro-7,8-dihydro[1,4]dioxino[2,3-g]quinazoline

HRID 596606Notes

Reaction equation

HRID 596606 reaction equation
[CH2:1]1[CH2:14][O:13][C:12]2[CH:11]=[C:10]3[C:5]([C:6](=O)[NH:7][CH:8]=[N:9]3)=[CH:4][C:3]=2[O:2]1.P(Cl)(Cl)([Cl:18])=O.N>>[Cl:18][C:6]1[C:5]2[C:10](=[CH:11][C:12]3[O:13][CH2:14][CH2:1][O:2][C:3]=3[CH:4]=2)[N:9]=[CH:8][N:7]=1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 24813Phosphorus oxychlorideHCID 1357365997,8-dihydro-[1,4]dioxino[2,3-g]quinazolin-4(3H)-one

Product 1

HCID 189328674-Chloro-7,8-dihydro[1,4]dioxino[2,3-g]quinazoline

Procedure

A mixture of 25.3 g. of 6,7-ethylenedioxyquinazolin-4(3H)-one and 50 ml. of phosphorus oxychloride is refluxed for 10 minutes, cooled, and added with stirring to one liter of ice. After addition of concentrated ammonia the resulting mixture is extracted with chloroform and the chloroform solution chromatographed through 300 mls. of silica gel while eluting with chloroform. Evaporation of the eluent yields 4-chloro-6,7-ethylenedioxyquinazoline, m.p. 169°-174° C.

Workup

  1. additionA mixture of 25.3 g
  2. temperaturecooled
  3. additionadded
  4. extractionis extracted with chloroform
  5. customthe chloroform solution chromatographed through 300 mls
  6. washof silica gel while eluting with chloroform
  7. customEvaporation of the eluent

Sources & evidence

ORD record
ord-407064169e0141268b4f6ee6e91dca4e
Source dataset
uspto-grants-1977_03
Patent number
US04011323

Reaction notes

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