Chloroform → HCID 69057860, compound
Reaction equation
Cl[C:2]([O:4][CH2:5][CH3:6])=[O:3].C(Cl)(Cl)Cl.Cl.Cl.[NH2:13][C:14]1[CH:25]=[CH:24][C:17]([CH2:18][N:19]([CH2:22][CH3:23])[CH2:20][CH3:21])=[CH:16][CH:15]=1.C(=O)([O-])O.[Na+]>C(N(CC)CC)C>[CH2:20]([N:19]([CH2:18][C:17]1[CH:16]=[CH:15][C:14]([NH:13][C:2](=[O:3])[O:4][CH2:5][CH3:6])=[CH:25][CH:24]=1)[CH2:22][CH3:23])[CH3:21]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
At 0° C., ethyl chloroformate (455 μL) was added to a chloroform solution (13 mL) of N-(4-aminobenzyl)-N,N-diethylamine dihydrochloride (1.0 g) obtained in Reference Example 2-1-(2) and triethylamine (2.2 mL), and stirred at 0° C. for 1.5 hours and then at room temperature for 2 hours. Aqueous sodium hydrogencarbonate solution was added to the reaction liquid to stop the reaction, and this was extracted with chloroform. The organic layer was washed with water and saturated saline water, and then dried with anhydrous sodium sulfate. The organic layer was concentrated under reduced pressure, and the residue was purified through silica gel column chromatography (chloroform/methanol=9/1) to obtain ethyl N-{4-[(diethylamino)methyl]phenyl}carbamate (530 mg) as an orange oily substance.
Workup
- waitat room temperature for 2 hours
- customthe reaction
- extractionthis was extracted with chloroform
- washThe organic layer was washed with water and saturated saline water
- dry with materialdried with anhydrous sodium sulfate
- concentrationThe organic layer was concentrated under reduced pressure
- customthe residue was purified through silica gel column chromatography (chloroform/methanol=9/1)
Sources & evidence
- ORD record
- ord-45ede95ce4b140ddb63c78ae4a6a3b4a
- Source dataset
- uspto-grants-2009_05
- Patent number
- US07531668B2
Reaction notes
Loading…