Phenyl isocyanate → HCID 20490672, compound

HRID 435061Notes

Reaction equation

HRID 435061 reaction equation
[CH3:1][C:2]1([CH3:19])[CH:6]([OH:7])[CH2:5][C:4]([CH2:10][O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)([CH2:8][CH3:9])[O:3]1.[C:20]1([N:26]=[C:27]=[O:28])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C1C=CC=CC=1.C(N(CC)CC)C>[CH3:19][C:2]1([CH3:1])[CH:6]([O:7][C:27]([NH:26][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:28])[CH2:5][C:4]([CH2:10][O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)([CH2:8][CH3:9])[O:3]1

Participants

5

Reactant 2

HCID 7672Phenyl isocyanateHCID 20490686HCID 20490686, compound

Product 1

HCID 20490672HCID 20490672, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 8471TriethylamineCatalystHCID 241BenzeneSolvent

Procedure

The alcohol of Example 3 (1 g) was dissolved in benzene (15 ml) and phenylisocyanate (600 mg) and a few drops of triethylamine were added. The mixture was refluxed for 20 hours. The solvent was then evaporated and the residue was taken up in ethyl acetate, washed with dilute hydrochloric acid and then with brine, dried over magnesium sulphate and evaporated down. The residue was purified on a silica column using 5% acetone in petrol as eluant. 1.4 g, corresponding to a 100% yield, of the desired product, as a viscous oil, were obtained. NMR showed the presence of both geometric isomers.

Workup

  1. temperatureThe mixture was refluxed for 20 hours
  2. customThe solvent was then evaporated
  3. washwashed with dilute hydrochloric acid
  4. dry with materialwith brine, dried over magnesium sulphate
  5. customevaporated down
  6. customThe residue was purified on a silica column

Sources & evidence

ORD record
ord-0d74ce0e79c84239bfec7afe56b2f38c
Source dataset
uspto-grants-1983_08
Patent number
US04400198

Reaction notes

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