Sodium Cyanide → HCID 21413815, compound

HRID 268493Notes

Reaction equation

HRID 268493 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:10][C:11]3[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=3[N:13]=2)=[C:5]([F:18])[CH:4]=1.[C-:19]#[N:20].[Na+]>CO>[O:10]1[C:11]2[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=2[N:13]=[C:9]1[C:6]1[CH:7]=[CH:8][C:3]([CH2:2][C:19]#[N:20])=[CH:4][C:5]=1[F:18]

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 21413843HCID 21413843, compound

Product 1

HCID 21413815HCID 21413815, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of 1.0 gm. of 2-(4-bromomethyl-2-fluorophenyl)benzoxazole in 50 cc. of dry methanol which has been cooled in an ice-water bath is added 1.5 gm. of sodium cyanide. The reaction mixture is stirred cold for 10 minutes, allowed to warm to room temperature and finally heated on the steam bath. Solution of the starting material occurs and after 5 minutes reflux the reaction mixture is cooled, concentrated to about 25 cc., and poured into 100 cc. of ice cold 2.5 N hydrochloric acid. The resulting precipitate is filtered and air dried to give crude 4-(benzoxazol-2-yl)-3-fluorophenylacetonitrile.

Workup

  1. additionTo a mixture of 1.0 gm
  2. additionis added 1.5 gm
  3. temperaturefinally heated on the steam bath
  4. waitSolution of the starting material occurs and after 5 minutes
  5. temperaturereflux the reaction mixture
  6. temperatureis cooled
  7. concentrationconcentrated to about 25 cc
  8. addition, and poured into 100 cc
  9. filtrationThe resulting precipitate is filtered
  10. customair dried

Sources & evidence

ORD record
ord-c7744113b73b4f0dbbefbb6636ed2f76
Source dataset
uspto-grants-1976_03
Patent number
US03947582

Reaction notes

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