Hydrochloric Acid → methyl 2-oxo-2,3-dihydro-1H-1,3-benzodiazole-5-carboxylate
Reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[C:6]([NH2:11])[CH:5]=1.C1C[O:16][CH2:15]C1.C(C1NC=CN=1)(C1NC=CN=1)=O.Cl>O>[CH3:1][O:2][C:3]([C:4]1[CH:9]=[CH:8][C:7]2[NH:10][C:15](=[O:16])[NH:11][C:6]=2[CH:5]=1)=[O:12]Participants
6
Conditions
- Temperature
- 23 °C
Procedure
To a solution of 3,4-diamino-benzoic acid methyl ester (5.00 g, 30.1 mmol) and THF (40 mL), was added carbonyl diimidazole (7.32 g, 45.1 mmol) at 0° C. The mixture stirred for 16 h, and allowed to warm to 23° C. A solution of 1M aq. HCl (50 mL) was added at 0° C., followed by water (70 mL) and the mixture was stirred for 1 h. The resulting precipitate was filtered and dried under reduced pressure for 18 h to yield the titled compound, which was used in the next step without further purification (5.45 g, 94%). MS (ESI/CI): mass calcd. for C9H8N2O3, 192.1; m/z found, 193.1 [M+H]+. 1H NMR (400 MHz, CDCl3): 11.01 (s, 1H), 10.84 (s, 1H), 7.63 (dd, J=8.2, 1.6 Hz, 1H), 7.47 (s, 1H), 7.02 (d, J=8.2 Hz, 1H), 3.82 (s, 3H).
Workup
- stirringthe mixture was stirred for 1 h
- filtrationThe resulting precipitate was filtered
- customdried under reduced pressure for 18 h
Sources & evidence
- ORD record
- ord-3413d624b77d4fd0ade2e4698fd52f46
- Source dataset
- uspto-grants-2014_10
- Patent number
- US08865713B2
Reaction notes
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