Benzene → HCID 53878279, compound

HRID 1863439Notes

Reaction equation

HRID 1863439 reaction equation
[O:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[N:11][OH:12])[CH2:3][CH2:2]1.C1C=CC=CC=1.[CH2:19]([N:21]=[C:22]=[O:23])[CH3:20]>C(N(CC)CC)C>[CH2:19]([NH:21][C:22]([O:12][N:11]=[C:4]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:10]=2[O:1][CH2:2][CH2:3]1)=[O:23])[CH3:20]

Participants

5

Reactant 3

HCID 241BenzeneHCID 8022Ethyl isocyanateHCID 44866984H-1-Benzopyran-4-one, 2,3-dihydro-, oxime

Product 1

HCID 53878279HCID 53878279, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

4-Chromanone oxime (20 g, 0.12 mole) was added to benzene (260 ml) and refluxed for 45 min. in a flask equipped with a Dean-Stark trap. The solution was cooled to 25°-30°, triethylamine (0.5 ml) was added, followed by ethyl isocyanate (8.5 g, 0.12 mole). The solution was refluxed for 3 hrs. and stored overnight at room temperature. The mixture was filtered and the filtrate was stripped of solvent under reduced pressure. Anhydrous ether (100 ml) was added to the residue and the mixture was cooled for 3 hrs. The product was collected by filtration, yield: 20 g (79%). A sample was recrystallized from isopropanol, m.p. 110°-111°.

Workup

  1. temperaturerefluxed for 45 min. in a flask
  2. customequipped with a Dean-Stark trap
  3. temperatureThe solution was cooled to 25°-30°
  4. temperatureThe solution was refluxed for 3 hrs
  5. filtrationThe mixture was filtered
  6. additionAnhydrous ether (100 ml) was added to the residue
  7. temperaturethe mixture was cooled for 3 hrs
  8. filtrationThe product was collected by filtration, yield: 20 g (79%)
  9. customA sample was recrystallized from isopropanol, m.p. 110°-111°

Sources & evidence

ORD record
ord-2b9a9674e2634571bf3d10dc449b1943
Source dataset
uspto-grants-1979_09
Patent number
US04169097

Reaction notes

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