Cyanide → HCID 19835675, compound
Reaction equation
Br[CH2:2][C:3]1[CH:10]=[CH:9][CH:8]=[C:7]([CH2:11]Br)[C:4]=1[C:5]#[N:6].CC1C=CC=C(C)C=1N.[C-]#N.[CH3:24][O-:25].[Na+].CN(C)[CH:29]=[O:30]>O>[CH3:24][O:25][CH2:2][C:3]1[CH:10]=[CH:9][CH:8]=[C:7]([CH2:11][O:30][CH3:29])[C:4]=1[C:5]#[N:6]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
2.0 g of 2,6-bis(bromomethyl)benzonitrile (F. Voegtle, P. Neumann, M. Zuber, Chem. Ber., 105, 2955 (1972)), prepared starting from 2,6-dimethylaniline by the Sandmayer reaction with cupreous cyanide and next by the bromination with N-bromosuccinimide,are dissolved in 2 ml of anhydrous N,N-dimethylformamide and added to the suspension of 1.24 g of sodium methylate in 10 ml of N,N-dimethylformamide at 0° C. After stirring the mixture for three hours at 0° C., the same is added with 20 ml of water and extracted with 120 ml of ethyl ether divided into three portions. The extracts, after drying with anhydrous sodium sulfate and evaporation to dryness, give a solid residue which, after sublimation at 100° C./0.04 Torr, gives 2,6-bis(methoxymethyl)benzonitrile with melting point 80°-81° C.; the yield obtained is 40%.
Workup
- extractionextracted with 120 ml of ethyl ether
- dry with materialThe extracts, after drying with anhydrous sodium sulfate and evaporation to dryness
- customgive a solid residue which
Sources & evidence
- ORD record
- ord-6cce4e5b34344952aa94994e89b647ab
- Source dataset
- uspto-grants-1989_12
- Patent number
- US04888283
Reaction notes
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