4-Cyanobenzaldehyde → HCID 21388866, compound

HRID 1606246Notes

Reaction equation

HRID 1606246 reaction equation
[CH3:1][O:2][C:3]([O:5][C:6]1[CH:12]=[CH:11][C:9]([NH2:10])=[CH:8][CH:7]=1)=[O:4].[C:13]([C:15]1[CH:22]=[CH:21][C:18]([CH:19]=O)=[CH:17][CH:16]=1)#[N:14].[O-2].[Al+3].[O-2].[O-2].[Al+3]>C1C=CC=CC=1>[C:3](=[O:4])([O:2][CH3:1])[O:5][C:6]1[CH:12]=[CH:11][C:9]([N:10]=[CH:19][C:18]2[CH:21]=[CH:22][C:15]([C:13]#[N:14])=[CH:16][CH:17]=2)=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 660424-CyanobenzaldehydeHCID 9989226AluminaHCID 21388859HCID 21388859, compound

Product 1

HCID 21388866HCID 21388866, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 0.835 g. of p-methoxycarbonyloxyaniline and 0.655 g. of p-cyanobenzaldehyde is gassed with argon in 50 ml. of benzene and heated under reflux for 1 hour (bath temperature 130°). The resulting water is separated with a water separator. During an additional hour, benzene condensed in the reflux condenser is now passed back into the reaction vessel through a layer of 20 g. of aluminium oxide (act. I). After cooling, the reaction mixture is freed from solvent in vacuum at 50°C. bath temperature, whereby there remain 1.395 g. of yellowish crystals which are recrystallized several times from isopropanol up to constant melting point and clearing point and up to the disappearance of side-products in the gas chromatogram. The pure, slightly yellowish p-[(p-cyanobenzyliden)amino]phenyl methyl carbonate obtained has a melting point of 145.1°-146.2° and a clearing point of 163.4°. UV (EtOH): ε270 = 20,250, ε324 = 10,800 (shoulders at 243 and 221 nm; minima at 312 and 233 nm).

Workup

  1. additionA mixture of 0.835 g
  2. temperatureunder reflux for 1 hour (bath temperature 130°)
  3. customThe resulting water is separated with a water separator
  4. waitDuring an additional hour
  5. custombenzene condensed in the reflux condenser
  6. temperatureAfter cooling
  7. customis freed from solvent in vacuum at 50°C.
  8. customof yellowish crystals which are recrystallized several times from isopropanol up to constant melting point and clearing point

Sources & evidence

ORD record
ord-58ddcc5add7f436ba9281604706439e9
Source dataset
uspto-grants-1976_04
Patent number
US03952046

Reaction notes

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