Ammonia → HCID 20470558, compound

HRID 1388244Notes

Reaction equation

HRID 1388244 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14](I)=[CH:13][CH:12]=2)=[CH:7][CH:6]=1.[CH3:18][N:19](C=O)C.N.C1(C)C=CC=CC=1>O>[CH3:1][O:2][CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([C:18]#[N:19])=[CH:13][CH:12]=2)=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 1140TolueneHCID 6228DimethylformamideHCID 20470550HCID 20470550, compound

Product 1

HCID 20470558HCID 20470558, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
149 °C

Procedure

Into a 200 ml three-neck flask were added 4'-(β-methyloxyethyl)-4-iodobiphenyl obtained in Step C (20 g, 0.59 mol), cuprous cyanide (6.2 g, 0.688 mol) and DMF (67 ml), and the mixture was reacted together under reflux with stirring at 149° C. for 6 hours. After completion of the reaction, the reaction liquid was cooled down to room temperature and 29% aqueous ammonia (20 ml) was added, followed by agitation. Toluene (50 ml) and water (100 ml) were then added and the reaction liquid was subjected to suction-filtration. The toluene layer of the filtrate was washed with 6 N-hydrochloric acid and then with sodium hydroxide aqueous solution and further with water till the layer became neutral. The resulting toluene layer was dried with anhydrous sodium sulfate (10 g), and passed through an active alumina layer, followed by distilling off toluene, recrystallizing the residual crystals from methanol (30 ml), filtering and drying to obtain objective 4'-(β-methyloxyethyl)-4-cyanobiphenyl (3 g) having a melting point (C-I point) of 50.7° C. When this product was mixed with 4'-octyloxy-4-cyanobiphenyl and the mixture was subjected to measurement for N→I point, its N→I point through extrapolation was -5° C. (With the above product alone, measurement of N→I point was impossible.) The values of the elemental analysis of the product accorded well with the calculated values thereof as follows:

Workup

  1. customthe mixture was reacted together
  2. temperatureunder reflux
  3. customAfter completion of the reaction
  4. customthe reaction liquid
  5. temperaturewas cooled down to room temperature
  6. customthe reaction liquid
  7. filtrationwas subjected to suction-filtration
  8. washThe toluene layer of the filtrate was washed with 6 N-hydrochloric acid
  9. dry with materialThe resulting toluene layer was dried with anhydrous sodium sulfate (10 g)
  10. distillationby distilling off toluene
  11. customrecrystallizing the residual crystals from methanol (30 ml)
  12. filtrationfiltering
  13. customdrying

Sources & evidence

ORD record
ord-f34dc1de3c9a4cbaa208a3341938492d
Source dataset
uspto-grants-1984_02
Patent number
US04431564

Reaction notes

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