2-Tolyl isocyanate → HCID 19735032, compound

HRID 326726Notes

Reaction equation

HRID 326726 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][C:14](=[O:16])[CH:13]([CH2:17][CH2:18][CH2:19][CH2:20][OH:21])[O:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[N:29]=[C:30]=[O:31]>C1(C)C=CC=CC=1.N1C=CC=CC=1.C(OCC)(=O)C>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][C:14](=[O:16])[CH:13]([CH2:17][CH2:18][CH2:19][CH2:20][O:21][C:30](=[O:31])[NH:29][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=2[CH3:22])[O:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 691942-Tolyl isocyanate2×HCID 19735037HCID 19735037, compound

Product 1

HCID 19735032HCID 19735032, compoundYield 97%

Reagents, catalysts & solvents 3

HCID 1049PyridineCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of N-benzyloxycarbonyl-5-(4-hydroxybutyl)-4-oxo-isoxazole (170 mg, 0.58 mmol) in dry toluene was added 2-methylphenyl isocyanate (76 μL, 0.61 mmol). The reaction mixture was heated at approximately 80° C. under nitrogen for 0.5 hour. One drop of pyridine was added and heating was continued for an additional 1.5 hours. A second portion (25 μL) of 2-methylphenyl isocyanate was added and the reaction mixture was heated for another 2 hours. The reaction mixture was then allowed to cool to ambient temperature and diluted with ethyl acetate and extracted with water. The aqueous layer was acidified with potassium hydrogen sulfate and extracted with ethyl acetate. The ethyl acetate solution was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to give 240 mg of the title compound. MS (FAB+) m/e 427 (M+H)+.

Workup

  1. temperatureheating
  2. temperaturethe reaction mixture was heated for another 2 hours
  3. temperatureto cool to ambient temperature
  4. extractionextracted with water
  5. extractionextracted with ethyl acetate
  6. washThe ethyl acetate solution was washed with brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bb6a55ba25d842a1ac5c974ba4db4ba5
Source dataset
uspto-grants-1993_12
Patent number
US05270302

Reaction notes

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