Hydrochloric Acid → HCID 67273003, compound
Reaction equation
[CH2:1]([C:3]([C:7]1[C:15]2[NH:14][C:13](=[O:16])[NH:12][C:11]=2[CH:10]=[CH:9][CH:8]=1)(O)[CH2:4][CH3:5])[CH3:2].Cl>[Pd].C(O)(=O)C>[CH2:1]([CH:3]([C:7]1[C:15]2[NH:14][C:13](=[O:16])[NH:12][C:11]=2[CH:10]=[CH:9][CH:8]=1)[CH2:4][CH3:5])[CH3:2]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 80 °C
Procedure
A mixture of 4-(1-ethyl-1-hydroxypropyl)-1,3-dihydro-2H-benzimidazol-2-one (32.9 g, 149 mmol), 10% palladium on carbon (50% wet; 3.3 g), concentrated hydrochloric acid (3 mL) and acetic acid (300 mL) was purged with hydrogen and stirred under balloon pressure hydrogen at 80° C. for 6 hr. The catalyst was removed by filtration, and the filter cake was washed with tetrahydrofuran. The filtrate was concentrated in vacuo. The residue was suspended in diisopropyl ether (25 ml), and the suspension was stirred at 70° C. for 30 min. n-Hexane (25 mL) was added to the suspension, cooled to room temperature and stirred for 30 min. The resulting solid was collected by filtration and washed with n-hexane to give the title compound (24.6 g, 120 mmol, 81%) as a colorless solid.
Workup
- customwas purged with hydrogen
- customThe catalyst was removed by filtration
- washthe filter cake was washed with tetrahydrofuran
- concentrationThe filtrate was concentrated in vacuo
- stirringthe suspension was stirred at 70° C. for 30 min. n-Hexane (25 mL)
- additionwas added to the suspension
- temperaturecooled to room temperature
- stirringstirred for 30 min
- filtrationThe resulting solid was collected by filtration
- washwashed with n-hexane
Sources & evidence
- ORD record
- ord-39a0c029c9034a1abfc8af7567ec2835
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08785460B2
Reaction notes
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