Ethylenediamine → 5-Cyano-2-(2,2,2-trifluoroethyl)-2-trifluoromethyl-1,3-benzodioxole
Reaction equation
Br[C:2]1[CH:19]=[CH:18][C:5]2[O:6][C:7]([CH2:13][C:14]([F:17])([F:16])[F:15])([C:9]([F:12])([F:11])[F:10])[O:8][C:4]=2[CH:3]=1.[Cu][C:21]#[N:22].NCCN>CN(C)C=O>[C:21]([C:2]1[CH:19]=[CH:18][C:5]2[O:6][C:7]([CH2:13][C:14]([F:17])([F:16])[F:15])([C:9]([F:12])([F:11])[F:10])[O:8][C:4]=2[CH:3]=1)#[N:22]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 160 °C
Procedure
35 g of the product of Example 24 were dissolved in 75 ml of dimethylformamide, and 10.5 g of copper(I) cyanide were added. The mixture was stirred for 8 hours at 160° C. The hot mixture was then discharged into 100 ml of ice-water, and 30 g of 1,2-diaminoethane were added. After stirring for 30 minutes, the organic phase was separated off and the aqueous phase was extracted with methylene chloride. The combined organic phases were washed with a solution of 30 g of 1,2-diaminoethane in 75 ml of water, dried over magnesium sulphate and distilled under high vacuum to give 20.5 g of product (=69% of theory). The. boiling point was 110° C. at 0.02 mbar. =19F NMR: -58.1 and -84.6 ppm. 1H NMR: 3.08 ppm.
Workup
- additionwere added
- stirringAfter stirring for 30 minutes
- customthe organic phase was separated off
- extractionthe aqueous phase was extracted with methylene chloride
- washThe combined organic phases were washed with a solution of 30 g of 1,2-diaminoethane in 75 ml of water
- dry with materialdried over magnesium sulphate
- distillationdistilled under high vacuum
Sources & evidence
- ORD record
- ord-3b6125c7f4fe4b728e99433e566e92b2
- Source dataset
- uspto-grants-1995_05
- Patent number
- US05420309
Reaction notes
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