N-[(2,4-dichloro-1,3-thiazol-5-yl)methylidene]hydroxylamine → 2,4-Dichloro-5-cyanothiazole
Reaction equation
[Cl:1][C:2]1[S:3][C:4]([CH:8]=[N:9]O)=[C:5]([Cl:7])[N:6]=1>C(OC(=O)C)(=O)C>[Cl:1][C:2]1[S:3][C:4]([C:8]#[N:9])=[C:5]([Cl:7])[N:6]=1Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 137 °C
Procedure
400 g (2.03 mol) of crude 2,4,-dichloro-5-thiazolecarboxaldehyde oxime (IV) are stirred with 2 liters of acetic anhydride at reflux temperature (137° C.) for 4 hours. Fractionation using a silvered distillation column 1 m long provided 271 g (=75.7% of theory) of 2,4-dichloro-5-thiazolecarbonitrile (V) at 112° C./20 m bar, this product being identical by mass and IR spectroscopy with that described in German Offenlegungsschrift No. 3,038,608 (which can also be named 2,4-dichloro-5-cyanothiazole). The compound solidifies at room temperature to give colourless crystals which can be recrystallized from petroleum ether. Melting point: 34°-35° C.
Workup
- distillationa silvered distillation column 1 m long provided 271 g (=75.7% of theory) of 2,4-dichloro-5-thiazolecarbonitrile (V) at 112° C./20 m bar
- customsolidifies at room temperature
- customto give colourless crystals which
- customcan be recrystallized from petroleum ether
Sources & evidence
- ORD record
- ord-181ad24b7c3042988f674c4f253ff3c3
- Source dataset
- uspto-grants-1985_11
- Patent number
- US04555577
Reaction notes
Loading…