Triethylamine → 3-(4-Methylbenzoyl)thiophen-2-amine
Reaction equation
[CH3:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([CH2:8][C:9]#[N:10])=[O:7])=[CH:4][CH:3]=1.[S:13]1CC(O)S[CH2:15][CH:14]1O.C(N(CC)CC)C>C(O)C>[NH2:10][C:9]1[S:13][CH:14]=[CH:15][C:8]=1[C:6]([C:5]1[CH:11]=[CH:12][C:2]([CH3:1])=[CH:3][CH:4]=1)=[O:7]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a suspension of 4-methylbenzoylacetonitrile (0.325 g; 2.042 mmol) and p-dithiane-2,5-diol (0.155 g; 1.018 mmol) in ethanol (4.3 mL) cooled at 0° C. was added triethylamine (0.283 mL; 2.042 mmol). After 10 min at room temperature, the reaction mixture was heated under reflux for 2 h. After cooling to room temperature, the reaction mixture was partitioned between ethyl acetate and water. The organic phase was washed with brine, dried over sodium sulphatesulphate, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel using a gradient of ethyl acetate (10-25%) in heptane to afford the title compound (0.288 g; 65%) as a yellow solid.
Workup
- temperaturethe reaction mixture was heated
- temperatureunder reflux for 2 h
- temperatureAfter cooling to room temperature
- customthe reaction mixture was partitioned between ethyl acetate and water
- washThe organic phase was washed with brine
- dry with materialdried over sodium sulphatesulphate
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customThe residue was purified by flash chromatography on silica gel using a gradient of ethyl acetate (10-25%) in heptane
Sources & evidence
- ORD record
- ord-d5fc8a55d4d84a2daa06bb9f151e5ed1
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08785638B2
Reaction notes
Loading…