4-Chlorophenyl Isocyanate → HCID 68143242, compound

HRID 1283958Notes

Reaction equation

HRID 1283958 reaction equation
[C:1]1(=[O:8])[CH2:6][CH2:5][CH2:4][C:3](=[O:7])[CH2:2]1.[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([N:16]=[C:17]=[O:18])=[CH:12][CH:11]=1.C(N(CC)CC)C.[N-]=C=O>CC(C)=O>[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17]([C:2]2[C:3](=[O:7])[CH2:4][CH2:5][CH2:6][C:1]=2[OH:8])=[O:18])=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 76934-Chlorophenyl IsocyanateHCID 8471TriethylamineHCID 104341,3-CyclohexanedioneHCID 105034Isocyanate

Product 1

HCID 68143242HCID 68143242, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution containing 8.5 parts of cyclohexane-1,3-dione, 11.5 parts of p-chlorophenylisocyanate and 7.6 parts of triethylamine in 200 parts of acetone is stirred and refluxed for two hours. The infrared spectrum then shows no isocyanate (band at 2270 cm-1). The solution is concentrated under reduced pressure to about 50 parts, with separation of a few crystals, and poured with stirring into 500 parts of 2-normal hydrochloric acid. The precipitated solid is collected by filtration and dried. The resulting solid is mixed with chloroform, 250 parts by volume, and filtered from 6.5 parts of insoluble by-product. Removal of chloroform from the filtrate leaves a light pink solid which is crystallized from alcohol to give 6.7 parts of nearly white solid, melting point 113°C.-114°C.

Workup

  1. temperaturerefluxed for two hours
  2. concentrationThe solution is concentrated under reduced pressure to about 50 parts, with separation of a few crystals
  3. additionpoured
  4. stirringwith stirring into 500 parts of 2-normal hydrochloric acid
  5. filtrationThe precipitated solid is collected by filtration
  6. customdried
  7. additionThe resulting solid is mixed with chloroform, 250 parts by volume
  8. filtrationfiltered from 6.5 parts of insoluble by-product
  9. customRemoval of chloroform from the filtrate
  10. customleaves a light pink solid which
  11. customis crystallized from alcohol
  12. customto give 6.7 parts of nearly white solid, melting point 113°C.-114°C.

Sources & evidence

ORD record
ord-97e3cb9baea445188a8628c2c60f7beb
Source dataset
uspto-grants-1976_08
Patent number
US03976785

Reaction notes

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