Sodium Cyanide → HCID 14461236, compound

HRID 2351863Notes

Reaction equation

HRID 2351863 reaction equation
Cl[CH2:2][C:3]1[CH:19]=[CH:18][C:6]([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=2)=[CH:5][CH:4]=1.[C-:20]#[N:21].[Na+]>O.C(O)C>[C:20]([CH2:2][C:3]1[CH:19]=[CH:18][C:6]([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=2)=[CH:5][CH:4]=1)#[N:21]

Participants

5

Reactant 2

HCID 8929Sodium CyanideHCID 14461232HCID 14461232, compound

Product 1

HCID 14461236HCID 14461236, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

In a 50 ml round-bottom two-necked flask, 2.0 g were suspended in 2.0 ml of water and heated to 80° C. A 9.2 g amount of 4-(4'-chloromethylbenzyl)benzotrifluoride was dissolved in 7.1 ml of ethanol. This solution was added dropwise into the NaCN suspension. The proportion of undissolved substances increased. The reaction mixture turned brown. The feedstock was boiled under reflux for 5 hours. After the reaction mixture had cooled down to room temperature, the solid substance was removed by filtration and washed with 30 ml ethanol. The filtration was concentrated in a rotary evaporator (bath temp. 30° C., water-jet vacuum). The oily residue was dissolved in 50 ml of diethyl ether and washed to neutrality four times with 30 ml of water each time. The organic phase was dried over sodium sulfate. The drying agent was removed by filtration and the ether was removed by distillation in a rotary evaporator (bath temp. 30° C., water-jet vacuum). The raw product (8.0 g) was chromatographed on silica gel 60 (0.63-0.200) with ether/pentane (1/4) and the 4-(4'-cyanomethylbenzyl)benzotrifluoride (5.8 g) thus obtained was recrystallized from 44 ml of solvent blend (petroleum benzin 60°-80°C0-diethyl ether 5:1 v/v). The precipitated crystallizate was removed by filtration via a D-4 glass suction funnel and washed with 25 ml of ice-cold petroleum benzin. The product was dried in a vacuum drying oven (oil pump) at room temperature for 5 hours.

Workup

  1. temperatureThe proportion of undissolved substances increased
  2. temperatureunder reflux for 5 hours
  3. temperatureAfter the reaction mixture had cooled down to room temperature
  4. customthe solid substance was removed by filtration
  5. washwashed with 30 ml ethanol
  6. filtrationThe filtration
  7. concentrationwas concentrated in a rotary evaporator (bath temp. 30° C., water-jet vacuum)
  8. dissolutionThe oily residue was dissolved in 50 ml of diethyl ether
  9. washwashed
  10. dry with materialThe organic phase was dried over sodium sulfate
  11. customThe drying agent was removed by filtration
  12. customthe ether was removed by distillation in a rotary evaporator (bath temp. 30° C., water-jet vacuum)
  13. customThe raw product (8.0 g) was chromatographed on silica gel 60 (0.63-0.200) with ether/pentane (1/4)

Sources & evidence

ORD record
ord-fdea2844a82340c9b39dd5d5d1434656
Source dataset
uspto-grants-1989_10
Patent number
US04874763

Reaction notes

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