Dimethylformamide → 3-Methoxy-1,2-thiazole-4-carbonitrile
Reaction equation
Br[C:2]1[C:3]([O:7][CH3:8])=[N:4][S:5][CH:6]=1.[CH3:9][N:10](C)C=O.[C-]#N.[Na+]>O>[C:9]([C:2]1[C:3]([O:7][CH3:8])=[N:4][S:5][CH:6]=1)#[N:10]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
To a solution of 38.8 g. (0.2 mole) of 4-bromo-3-methoxyisothiazole prepared as in Example 15 in 80 ml. of dimethylformamide was added 54 g. (0.6 mole) of cuprous cyanide. The mixture was stirred and heated at reflux for 1 hour. Then the reaction mixture was cooled to 25° C., and 40 g. (0.81 mole) of sodium cyanide in 120 ml. of water was added in portions. The mixture exothermed to 60°-70° C. and was allowed again to cool to 25° C. The reaction solution was then extracted thoroughly with ether. The ether extracts were washed with 10% sodium cyanide solution and then water. After drying over anhydrous magnesium sulfate and evaporation 23.4 g. (83%) of 4-cyano-3-methoxyisothiazole was obtained as a white solid, m.p. 60°-62° C. after crystallization from ligroin (90°-120°).
Workup
- temperatureheated
- temperatureat reflux for 1 hour
- customexothermed to 60°-70° C.
- temperatureto cool to 25° C
- extractionThe reaction solution was then extracted thoroughly with ether
- washThe ether extracts were washed with 10% sodium cyanide solution
- dry with materialAfter drying over anhydrous magnesium sulfate and evaporation 23.4 g
Sources & evidence
- ORD record
- ord-63c13e5dfd134b64be575a5a0edf8e08
- Source dataset
- uspto-grants-1977_10
- Patent number
- US04053479
Reaction notes
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