Ethyl Acetate → HCID 12912438, compound
Reaction equation
NC1[C:3](=[CH:8][C:9]([C:14]([O:16][CH2:17][CH3:18])=[O:15])(C)CC=1C)C(OC)=O.[C:19]1([N:25]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:26]=[NH:27])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(OCC)(=[O:36])C>>[CH2:17]([O:16][C:14]([C:9]1[C:8]([CH3:3])=[C:24]2[C:23](=[CH:22][C:21]=1[CH3:20])[N:27]=[CH:26][N:25]([C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)[C:19]2=[O:36])=[O:15])[CH3:18]Participants
Conditions
- Temperature
- 200 °C
Procedure
In an open flask a mixture consisting of 600 mg of methyl 2-amino-5-ethoxycarbonyl-3,5-dimethylbenzoate and 850 ml of N,N-diphenylformamidine was heated to 200° C. with occasional swirling. The temperature of the reaction mixture was maintained at around 200° C. for 1.5 hours. After cooling, the mixture was taken up in ethyl acetate, and the ethyl acetate extract was washed successively with dilute hydrochloric acid and water, and dried over sodium sulfate. The solvent was removed by evaporation. Chromatography on silica gel column and recrystallization from ethanol/water yielded 556 mg (71.9% of theory) of 6-ethoxycarbonyl-5,7-dimethyl-3-phenyl-4(3H)-quinazolinone melting at 102°-103° C. 1H NMR: (CDCl3) 1.43 (t, 3H), 2.48 (s, 3H), 2.83 (s, 3H), 4.48 (q, 2H), 7.30-7.90 (m, 6H), 8.14 (s, 1H).
Workup
- temperatureThe temperature of the reaction mixture was maintained at around 200° C. for 1.5 hours
- temperatureAfter cooling
- extractionthe ethyl acetate extract
- washwas washed successively with dilute hydrochloric acid and water
- dry with materialdried over sodium sulfate
- customThe solvent was removed by evaporation
- customChromatography on silica gel column and recrystallization from ethanol/water
Sources & evidence
- ORD record
- ord-b77bd6edfdf845048dd64ac2d03faace
- Source dataset
- uspto-grants-1981_06
- Patent number
- US04276295
Reaction notes
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