Formic Acid → 3-Propyl-1H-quinazoline-2,4-dione
Reaction equation
[CH2:1]([N:4]=[C:5]=[O:6])[CH2:2][CH3:3].[C:7](OCC)(=[O:15])[C:8]1[C:9](=[CH:11][CH:12]=[CH:13][CH:14]=1)[NH2:10].C[O-].[Na+].C(O)=O>C1(C)C(C)=CC=CC=1.C(O)C.CO>[CH2:1]([N:4]1[C:7](=[O:15])[C:8]2[C:9](=[CH:11][CH:12]=[CH:13][CH:14]=2)[NH:10][C:5]1=[O:6])[CH2:2][CH3:3]Participants
Conditions
- Temperature
- 110 °C
Procedure
A solution of propyl isocyanate (34.0 g, 0.40 mol) in xylene (100 ml) is metered, at room temperature, into a solution of ethyl anthranilate (66.1 g, 0.40 mol) in xylene (200 ml). After the addition has ended, the batch is stirred at 110° C. for 2 hours. 7.20 ml of a 30% solution of methanolic sodium methylate (0.040 ml) are metered in and the mixture is stirred at 90° C. for a further 2 hours, during which process methanol and ethanol are distilled off. 3.6 ml of 85% formic acid (0.080 mol) are subsequently added and the mixture is stirred at 90° C. for a further hour. After cooling, the product is filtered off with suction, washed with 3×25 ml of xylene, 3×25 ml of ethanol and 3×25 ml of water, and dried. 67.3 g of 3-(propyl)-2,4(1H,3H)-quinazolinedione (yield: 82.4% of theory) of melting point 190° to 191° C. (lit. 187° to 188° C.) are obtained.
Workup
- additionAfter the addition
- stirringis stirred at 90° C. for a further 2 hours, during which
- distillationare distilled off
- stirringthe mixture is stirred at 90° C. for a further hour
- temperatureAfter cooling
- filtrationthe product is filtered off with suction
- washwashed with 3×25 ml of xylene, 3×25 ml of ethanol and 3×25 ml of water
- customdried
Sources & evidence
- ORD record
- ord-83b32eef86574ba28e293afb948c0fb5
- Source dataset
- uspto-grants-1998_01
- Patent number
- US05710319
Reaction notes
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