Hydrochloric Acid → HCID 15444379, compound
Reaction equation
Cl.C([NH:5][C:6]1[C:7](=[O:17])[O:8][C:9]2[C:14]([CH:15]=1)=[CH:13][C:12]([NH2:16])=[CH:11][CH:10]=2)(=O)C>C(O)C>[NH2:5][C:6]1[C:7](=[O:17])[O:8][C:9]2[C:14]([CH:15]=1)=[CH:13][C:12]([NH2:16])=[CH:11][CH:10]=2Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 4 °C
Procedure
To a solution composed of 12.63 mL of 12 M hydrochloric acid in 6.32 mL ethanol was added 0.919 g (4.2 mmol) of compound 2. The solution was heated to reflux for 30 min and then cooled to 4° C. overnight. The resulting precipitate was removed by filtration and dissolved in a minimal volume of distilled water. The solution was neutralized by addition of 25% ammonium hydroxide and cooled at 4° C. for three hours. The resulting precipitate was removed by filtration and recrystallized from water to give a yellow compound (3) (0.484 g, 2.7 mmol) in 65% yield. mp 183-186° C. (lit: 183-184° C.). FTIR (KBr) (cm−1): 3420, 3340, 1690, 1635. 1H-NMR (DMSO-d6): δ (ppm) 6.95 (d, J=8.5 Hz, 1H), 6.56 (s, 1H), 6.49 (d, J=2.4 Hz, 1H), 6.46 (dd, J=10.0 Hz, J=2.6 Hz, 1H), 5.48 (bs, 2H), 5.00 (bs, 2H). 13C-NMR (DMSO-d6): δ (ppm) 159.95, 146.50, 141.19, 134.13, 123.04, 116.75, 113.70, 109.30, 108.42. HRMS expected: 177.05920; found: 177.05979.
Workup
- temperatureThe solution was heated
- temperatureto reflux for 30 min
- customThe resulting precipitate was removed by filtration
- dissolutiondissolved in a minimal volume of distilled water
- additionThe solution was neutralized by addition of 25% ammonium hydroxide
- temperaturecooled at 4° C. for three hours
- customThe resulting precipitate was removed by filtration
- customrecrystallized from water
Sources & evidence
- ORD record
- ord-abb6977bfe7e4b75b43a3bd910b748e0
- Source dataset
- uspto-grants-2010_04
- Patent number
- US07700375B2
Reaction notes
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