Allyl isocyanate → HCID 54033309, compound

HRID 1863440Notes

Reaction equation

HRID 1863440 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.[CH2:13]([N:16]=[C:17]=[O:18])[CH:14]=[CH2:15]>C(N(CC)CC)C.C1C=CC=CC=1>[CH2:13]([NH:16][C:17]([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:18])[CH:14]=[CH2:15]

Participants

5

Reactant 2

HCID 15123Allyl isocyanateHCID 44866984H-1-Benzopyran-4-one, 2,3-dihydro-, oxime

Product 1

HCID 54033309HCID 54033309, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 8471TriethylamineCatalystHCID 241BenzeneSolvent2×

Procedure

A solution containing 6.52 g (0.04 mole) of 4-chromanone oxime and 75 ml benzene was stirred and refluxed for 0.50 hrs. using a Dean-Stark apparatus. The solution was cooled to 60° and 6 drops triethylamine and 3.32 g (0.04 mole) allyl isocyanate in 10 ml benzene was added. The solution was stirred and refluxed for 4 hrs., concentrated to dryness, and the residue was recrystallized from 20 ml toluene to give 7.15 g (73%) of the product, m.p. 83°-86°.

Workup

  1. temperaturerefluxed for 0.50 hrs
  2. temperatureThe solution was cooled to 60°
  3. stirringThe solution was stirred
  4. temperaturerefluxed for 4 hrs
  5. concentration, concentrated to dryness
  6. customthe residue was recrystallized from 20 ml toluene

Sources & evidence

ORD record
ord-ff709704c7d1485590b09a0f14813ba8
Source dataset
uspto-grants-1979_09
Patent number
US04169097

Reaction notes

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