Pyridine → 3-(N Ethyloxycarbonyl 1,4 dihydro-4 pyridyl)-2-(4-methoxyphenyl)6,7-dihydro [5H]-pyrrolo[1,2-a]imidazole
Reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[C:11]3[CH2:16][CH2:15][CH2:14][N:12]3[CH:13]=2)=[CH:5][CH:4]=1.[N:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.Cl[C:24]([O:26][CH2:27][CH3:28])=[O:25].C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[CH2:27]([O:26][C:24]([N:17]1[CH:22]=[CH:21][CH:20]([C:13]2[N:12]3[CH2:14][CH2:15][CH2:16][C:11]3=[N:10][C:9]=2[C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)[CH:19]=[CH:18]1)=[O:25])[CH3:28]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
A stirred solution of 2.8 g (13.1 mmoles) of 2-(4-methoxyphenyl)-6,7-dihydro-[5H]-pyrrolo[1,2-a]imidazole, prepared as described above, and 6.2 g (78.4 mmoles) of dry pyridine in 30 ml of dry CH2Cl2 was treated dropwise over 1 hour at 5° C. under argon atmosphere with 4.25 g (39.2 mmoles) of ethyl chloroformate. After stirring for 1 hour an additional 3.1 g (39.2 mmoles) of pyridine was added, followed by 2.15 g (19.8 mmoles) of ethyl chloroformate added over 2 hours. The mixture was stirred overnight at 25° C., then poured into ice water made alkaline with Na2CO3 and extracted with CH2Cl2. The organic phase was sequentially washed with 0.2 N HCl, water, and aqueous K2CO3 solution, dried over Na2SO4 and stripped in vacuo to afford the titled compound as an amber resin.
Workup
- additionwas added
- additionadded over 2 hours
- extractionextracted with CH2Cl2
- washThe organic phase was sequentially washed with 0.2 N HCl, water, and aqueous K2CO3 solution
- dry with materialdried over Na2SO4
Sources & evidence
- ORD record
- ord-7f9809bd04bf47878496cceaa6bace82
- Source dataset
- uspto-grants-1988_06
- Patent number
- US04751310
Reaction notes
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