Oxalyl chloride → 6-Methoxy-7-nitroquinazoline-2,4(1H,3H)-dione
Reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[C:8]([O:14][CH3:15])=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].C(Cl)(=O)[C:17](Cl)=[O:18]>O1CCCC1.C(Cl)(Cl)Cl>[CH3:15][O:14][C:8]1[CH:7]=[C:3]2[C:2](=[CH:10][C:9]=1[N+:11]([O-:13])=[O:12])[NH:1][C:17](=[O:18])[NH:6][C:4]2=[O:5]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 60 °C
Procedure
108 mg (0.5 mmol) of 2-amino-5-methoxy-4-nitrobenzamide were dissolved in 5 ml of tetrahydrofuran and 5 ml of chloroform, and oxalyl chloride (solution in toluene) was added. The mixture was stirred at 60° C. for 5 hours and then concentrated in vacuo. Addition of toluene was followed by renewed concentration. 120 mg (100%) of the desired product were obtained.
Workup
- concentrationconcentrated in vacuo
- additionAddition of toluene
- concentrationconcentration
Sources & evidence
- ORD record
- ord-013b2269be7a45b5ae5308ee0da1ac3e
- Source dataset
- uspto-grants-2012_08
- Patent number
- US08247452B2
Reaction notes
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