Oxalyl chloride → 6-Methoxy-7-nitroquinazoline-2,4(1H,3H)-dione

HRID 855797Notes

Reaction equation

HRID 855797 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

HCID 65578Oxalyl chlorideHCID 688067432-Amino-5-methoxy-4-nitrobenzamide

Product 1

HCID 688048116-Methoxy-7-nitroquinazoline-2,4(1H,3H)-dioneYield 100%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent

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

  1. concentrationconcentrated in vacuo
  2. additionAddition of toluene
  3. concentrationconcentration

Sources & evidence

ORD record
ord-790bbb3f2e5843329c85dbcece6f39b2
Source dataset
uspto-grants-2007_08
Patent number
US07262220B2

Reaction notes

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