Ethyl bromoacetate → 3,3-dichloro-1-ethoxycarbonylmethyl-2,3,4,5-tetrahydro-1H-[1]benzazepin-2-one
Reaction equation
[Cl:1][C:2]1([Cl:14])[CH2:8][CH2:7][C:6]2[CH:9]=[CH:10][CH:11]=[CH:12][C:5]=2[NH:4][C:3]1=[O:13].Br[CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18].[H-].[Na+]>O1CCCC1>[Cl:14][C:2]1([Cl:1])[CH2:8][CH2:7][C:6]2[CH:9]=[CH:10][CH:11]=[CH:12][C:5]=2[N:4]([CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:3]1=[O:13]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 3,3-dichloro-2,3,4,5-tetrahydro-1H-[1]benzazepin-2-one (1.0 g, 4.32 mmol) and ethyl bromoacetate (0.51 ml) in of tetrahydrofuran (30 ml) was added dropwise with stirring during 15 minutes to a solution of sodium hydride (4.76 mmol) in tetrahydrofuran (20 ml) at room temperature under a nitrogen atmosphere. Stirring was continued for an additional 2 hours. The solution was quenched by addition of saturated aqueous ammonium chloride and the solvents were removed under reduced pressure. The residue was extracted with ether (3×20 ml), and the combined ether solutions washed with saturated brine (20 ml) and dried over magnesium sulfate. Removal of the solvent under reduced pressure gave 3,3-dichloro-1-ethoxycarbonylmethyl-2,3,4,5-tetrahydro-1H-[1]benzazepin-2-one. NMR(CDCl3):δ1.27 (t, 3H); 3.22 (m, 4H); 4.25 (q, 2H); 4.65 (s, 2H), 7.3 (m, 4H).
Workup
- customThe solution was quenched by addition of saturated aqueous ammonium chloride
- customthe solvents were removed under reduced pressure
- extractionThe residue was extracted with ether (3×20 ml)
- washthe combined ether solutions washed with saturated brine (20 ml)
- dry with materialdried over magnesium sulfate
- customRemoval of the solvent under reduced pressure
Sources & evidence
- ORD record
- ord-a8676c4667f1459b86f4e9854ef583f1
- Source dataset
- uspto-grants-1983_10
- Patent number
- US04410520
Reaction notes
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