Water → HCID 54445525, compound

HRID 1863438Notes

Reaction equation

HRID 1863438 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[O:9][CH2:8][CH2:7][C:6]2=[N:13][OH:14].O.[CH2:16]([N:18]=[C:19]=[O:20])[CH3:17]>C1C=CC=CC=1.CCOCC>[CH2:16]([NH:18][C:19]([O:14][N:13]=[C:6]1[C:5]2[CH:4]=[C:3]([O:2][CH3:1])[CH:12]=[CH:11][C:10]=2[O:9][CH2:8][CH2:7]1)=[O:20])[CH3:17]

Participants

6

Reactant 3

HCID 962WaterHCID 8022Ethyl isocyanateHCID 85960732HCID 85960732, compound

Product 1

HCID 54445525HCID 54445525, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

A 42 g (0.22 mole) portion of 6-methoxy-4-chromanone oxime in 600 ml of benzene was refluxed until all water was removed via a Dean-Stark trap. The solution was treated with 1 ml of triethylamine, followed by the dropwise addition of 14 g (0.20 mole) of ethyl isocyanate at reflux. The reaction mixture was refluxed for 4 hrs., stored overnight at room temperature, and stripped of benzene under reduced pressure. The viscous residue was taken up in 250 ml of ether, refrigerated 6 hrs., and filtered. The cream colored solid was washed with 150 ml of ether and dried, m.p. 97°-98°. Yield: 44 g (83%).

Workup

  1. customwas removed via a Dean-Stark trap
  2. additionThe solution was treated with 1 ml of triethylamine
  3. temperatureat reflux
  4. temperatureThe reaction mixture was refluxed for 4 hrs
  5. filtration, and filtered
  6. washThe cream colored solid was washed with 150 ml of ether
  7. customdried

Sources & evidence

ORD record
ord-6b587707b6f7408695768e1eff7a512f
Source dataset
uspto-grants-1979_09
Patent number
US04169097

Reaction notes

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