Phosphorus oxychloride → 4-Chloro-7-ethylamino-6-nitroquinazoline
Reaction equation
[CH2:1]([NH:3][C:4]1[CH:13]=[C:12]2[C:7]([C:8](=O)[NH:9][CH:10]=[N:11]2)=[CH:6][C:5]=1[N+:15]([O-:17])=[O:16])[CH3:2].P(Cl)(Cl)([Cl:20])=O.C(=O)([O-])O.[Na+]>>[Cl:20][C:8]1[C:7]2[C:12](=[CH:13][C:4]([NH:3][CH2:1][CH3:2])=[C:5]([N+:15]([O-:17])=[O:16])[CH:6]=2)[N:11]=[CH:10][N:9]=1Participants
Conditions
- Temperature
- 110 °C
Procedure
7-Ethylamino-6-nitro-4(3H)-quinazolinone (30.0 g, 128 mmol) was suspended in phosphorus oxychloride (270 ml, 2.90 mol) and the mixture was heated at 110° C. for 2 hours under an argon gas atmosphere (to form a clear solution). After it was confirmed that the starting material disappeared, unreacted phosphorus oxychloride was removed under reduced pressure. After the residue was subjected to azeotrope with toluene, the resulting oily substances were dissolved in the necessary minimum amount of tetrahydrofuran. The tetrahydrofuran solution obtained was poured onto ice-cold water by adding a sufficient amount of sodium hydrogen carbonate, followed by extraction with ethyl acetate. The organic layer was dried (over anhydrous magnesium sulfate), and the drying agent was filtered off. The filtrate was concentrated under reduced pressure to give the title compound (33.4 g).
Workup
- customto form a clear solution)
- customunreacted phosphorus oxychloride was removed under reduced pressure
- dissolutionthe resulting oily substances were dissolved in the necessary minimum amount of tetrahydrofuran
- customThe tetrahydrofuran solution obtained
- additionwas poured onto ice-cold water
- extractionfollowed by extraction with ethyl acetate
- dry with materialThe organic layer was dried (over anhydrous magnesium sulfate)
- filtrationthe drying agent was filtered off
- concentrationThe filtrate was concentrated under reduced pressure
Sources & evidence
- ORD record
- ord-fb7b1f6169ea4254bc8191800e2d83d2
- Source dataset
- uspto-grants-2000_10
- Patent number
- US06127541
Reaction notes
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