Triethylamine → HCID 8112552, compound
Reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:9]([Br:12])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].C(N(CC)CC)C.[C:20]1([CH2:26][CH2:27][C:28](Cl)=[O:29])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>ClCCl>[Br:12][C:9]1[CH:10]=[CH:11][C:2]([NH:1][C:28](=[O:29])[CH2:27][CH2:26][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[C:3]([CH:8]=1)[C:4]([O:6][CH3:7])=[O:5]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
Into a 100-mL round-bottom flask, was placed a solution of methyl 2-amino-5-bromobenzoate (5.0 g, 21.73 mmol), triethylamine (4.39 g, 43.38 mmol) and 3-phenylpropanoyl chloride (3.67 g, 21.76 mmol) in dichloromethane (50 mL). The resulting mixture was stirred for 12 hours at room temperature. The reaction was then quenched by the addition of 50 mL of water. The resulting mixture was extracted with 3×50 mL of dichloromethane. The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated under vacuum. The residue was purified by chromatography over a silica gel column with ethyl acetate/petroleum ether (2:1) to provide the title compound as a white solid.
Workup
- customInto a 100-mL round-bottom flask, was placed
- customThe reaction was then quenched by the addition of 50 mL of water
- extractionThe resulting mixture was extracted with 3×50 mL of dichloromethane
- dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
- filtrationfiltered
- concentrationconcentrated under vacuum
- customThe residue was purified by chromatography over a silica gel column with ethyl acetate/petroleum ether (2:1)
Sources & evidence
- ORD record
- ord-52acfdfa7f7349c2bc66c17b6bf42654
- Source dataset
- uspto-grants-2015_12
- Patent number
- US09221804B2
Reaction notes
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