Ethanol → HCID 67869955, compound
Reaction equation
C([CH2:3][NH:4][C:5]([C:7]1[S:11][C:10]([CH3:12])=[N:9][C:8]=1[CH3:13])=[O:6])#N.BrBr.C(O)C.[CH2:19]([N:21](CC)CC)C.C([O:29][CH2:30][CH3:31])(=O)C>O>[C:19]([CH:30]([O:29][CH2:3][NH:4][C:5]([C:7]1[S:11][C:10]([CH3:12])=[N:9][C:8]=1[CH3:13])=[O:6])[CH3:31])#[N:21]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
1.0 g of N-cyanomethyl-2,4-dimethylthiazole-5-carboxylic acid amide was dissolved in 30 ml of ethyl acetate. Bromine (0.3 ml) was added and the mixture was heated under reflux until the dark brown color of bromine disappeared. The reaction mixture was cooled over an ice bath, and 1.0 g of ethanol, 2.0 g of triethylamine and 10 ml of ethyl acetate were added at the above temperature. The mixture was stirred at room temperature for 2 hours. The reaction mixture was poured into water and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried, and distilled under reduced pressure to remove the solvent. The residue was purified by silica gel column chromatography. Elution with hexane/ethyl acetate gave 0.53 g (yield 43.1%) of the desired N-(alpha- cyano-alpha-ethoxymethyl)-2,4-dimethylthiazole5-carboxylic acid amide.
Workup
- temperaturethe mixture was heated
- temperatureThe reaction mixture was cooled over an ice bath
- extractionextracted with ethyl acetate
- washThe ethyl acetate layer was washed with water
- customdried
- distillationdistilled under reduced pressure
- customto remove the solvent
- customThe residue was purified by silica gel column chromatography
- washElution with hexane/ethyl acetate
Sources & evidence
- ORD record
- ord-039d2e1f168847c796deb0b9e4878068
- Source dataset
- uspto-grants-1992_04
- Patent number
- US05104886
Reaction notes
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