Glycine → 1-Methyl-3,4-dihydro-1H-1,4-benzodiazepine-2,5-dione

HRID 1946641Notes

Reaction equation

[CH3:1][N:2]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[C:5](=[O:12])[O:4][C:3]1=O.[NH2:14][CH2:15]C(O)=O.O.C(N(CC)CC)C>COCCOC.C(O)(=O)C.CCOCC>[CH3:1][N:2]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[C:5](=[O:12])[NH:14][CH2:15][C:3]1=[O:4]

Participants

Conditions

Temperature: 60 °C

Procedure

1-Methyl-1H-benzo[d][1,3]oxazine-2,4-dione (11.0 g, 62.1 mmol) and 2-aminoacetic acid (5.13 g, 68.3 mmol) were dissolved in DME (60 mL) and water (20 mL) and triethylamine was added. The reaction mixture was stirred at 60° C. for 4 hours. The mixture was concentrated in vacuo to get a light tan heavy oily residue that was dissolved in acetic acid (75 mL). This mixture was refluxed 4 hours then cooled down to room temperature. The solvent was evaporated to get a tan heavy oil. The oil was allowed to stand at room temperature overnight in ether (50 mL). The beige crystalline solid was filtered and washed with ether. The solid was then triturated in ether to afford title compound 467 (7.95 g, 67%) as a beige crystalline solid. 1H NMR (DMSO-d6) δ (ppm): 8.70 (s, 1H), 7.70 (d, J=7.6 Hz, 1H), 7.60 (t, J=7.2 Hz, 1H), 7.42 (d, J=8.0 Hz, 1H), 7.32 (t, J=7.5 Hz, 1H), 3.75-3.72 (m, 1H), 3.51-3.46 (m, 1H), 3.28 (s, 3H). MS (ESI): 190.90 (MH)+

Workup

concentrationThe mixture was concentrated in vacuo
customto get a light tan heavy oily residue that
temperatureThis mixture was refluxed 4 hours
temperaturethen cooled down to room temperature
customThe solvent was evaporated
customto get a tan heavy oil
filtrationThe beige crystalline solid was filtered
washwashed with ether
customThe solid was then triturated in ether

Sources & evidence

ORD record: ord-fe4825a425f546a1b2849b214977a74c
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08399452B2

Reaction notes

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