Phenyl isocyanate → HCID 70017425, compound

HRID 726987Notes

Reaction equation

HRID 726987 reaction equation
[C@@H:1]12[C:7](=[O:8])[NH:6][C@@H:5]1[CH2:4][CH2:3][NH:2]2.[C:9]1([N:15]=[C:16]=[O:17])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C(Cl)(Cl)Cl.C(N(CC)CC)C>[O:8]=[C:7]1[C@@H:1]2[C@@H:5]([CH2:4][CH2:3][N:2]2[C:16](=[O:17])[NH:15][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[NH:6]1

Participants

5

Reactant 2

HCID 7672Phenyl isocyanateHCID 10820492(1S,5R)-2,6-Diazabicyclo[3.2.0]heptan-7-one

Product 1

HCID 70017425HCID 70017425, compound

Reagents, catalysts & solvents 2

HCID 8471TriethylamineCatalystHCID 6212ChloroformSolvent

Procedure

100 mg (0.89 mmol) of (1S,5R)-2,6-diazabicyclo[3.2.0]heptan-7-one were dissolved in 5 ml of chloroform and heated to boiling under reflux. Phenyl isocyanate (0.1 ml, 0.89 mmol) and 1 drop of triethylamine were added thereto and the mixture was left to react at the boiling temperature for 1 hour. After concentration the residue was chromatographed over silica gel (0.063-0.2 mm particle size) with ethyl acetate:ethanol=3:2.

Workup

  1. temperatureheated
  2. temperatureunder reflux
  3. waitthe mixture was left
  4. customto react at the boiling temperature for 1 hour
  5. concentrationAfter concentration the residue
  6. customwas chromatographed over silica gel (0.063-0.2 mm particle size) with ethyl acetate

Sources & evidence

ORD record
ord-81b984b3348b4c958a35fb84b61735a6
Source dataset
uspto-grants-1998_01
Patent number
US05712268

Reaction notes

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