Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Methyl Anthranilate | HCID 8635 | — |
| Reactant | Benzyl isocyanate | HCID 76639 | — |
| Reactant | HCID 710807 | HCID 710807 | — |
| Solvent | O-Xylene | HCID 7237 | — |
| Product | HCID 6458126 | HCID 6458126 | 81.3% |
Reaction Steps
A solution of benzyl isocyanate (13.3 g, 0.10 mol) in xylene (40 ml) is metered, at room temperature, into a solution of methyl anthranilate (15.1 g, 0.10 mol) in xylene (80 ml). After the addition has ended, the batch is stirred at 110° C. for 2 hours. Triethylamine (1.4 ml, 1.01 g, 0,010 mol) is added. The mixture is stirred at 90° C. for a further 2 hours. The desired cyclization product 3-(benzyl)-2,4(1H,3H)-quinazolinedione cannot be detected in the reaction solution by thin-layer chromatography. After cooling, the precipitate is filtered off with suction, washed with 3×25 ml of xylene and dried. 23.1 g of methyl N-(benzylcarbamoyl)anthranilate (yield: 81.3% of theory) of melting point 140° to 141° C. (lit. 139° to 140° C.) are obtained.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US05710319 |
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| Source dataset | uspto-grants-1998_01 |
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| ORD ID | ord-9c8c94b1bf6d4f5686896b0cc8c6e1fe |
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| Source note | uspto-grants-1998_01 |
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