Benzene → HCID 21404284, compound

HRID 972455Notes

Reaction equation

HRID 972455 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]1C=CC(C=O)=CC=1)#[N:14].[O-2].[Al+3].[O-2].[O-2].[Al+3].[CH:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>>[C:3](=[O:4])([O:2][CH3:1])[O:5][C:6]1[CH:12]=[CH:11][C:9]([N:10]=[C:15]([C:13]#[N:14])[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[CH:8][CH:7]=1

Participants

5

Reactant 4

HCID 241BenzeneHCID 660424-CyanobenzaldehydeHCID 9989226AluminaHCID 21388859HCID 21388859, compound

Product 1

HCID 21404284HCID 21404284, compound

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 aluminum 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 sideproducts in the gas chromatogram. The pure, slightly yellowish 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): ε 270 = 20250, ε 324 = 10800 (shoulders at 243 l 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-567ff432e8ea495fa53cbbb3b345c338
Source dataset
uspto-grants-1977_10
Patent number
US04053431

Reaction notes

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