Phenyl isocyanate → HCID 23121998, compound

HRID 1713518Notes

Reaction equation

HRID 1713518 reaction equation
[C:1]1([C:7]2([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:11]3[CH2:12][NH:13][CH2:14][CH2:15][N:10]3[C:9](=[O:16])[O:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:23]1([N:29]=[C:30]=[O:31])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C1(C)C=CC=CC=1>[O:16]=[C:9]1[N:10]2[CH2:15][CH2:14][N:13]([C:30]([NH:29][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[O:31])[CH2:12][CH:11]2[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[O:8]1

Participants

4

Reactant 2

HCID 7672Phenyl isocyanateHCID 231218811,1-Diphenyltetrahydro-1H-oxazolo[3,4-a]pyrazin-3(5H)-one

Product 1

HCID 23121998HCID 23121998, compoundYield 100.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of hexahydro-1,1-diphenyl-3H-oxazolo[3,4-a]pyrazin-3-one (85 mg, 0.29 mmol) in toluene (3 mL) was added phenyl isocyanate (70 mg, 0.59 mmol), and the mixture was stirred at 60° C. for 4 hours. The reaction solution was concentrated. Then, the residue was purified with silica gel column chromatography (hexane:ethyl acetate=2:1) and crystallized from diisopropyl ether to obtain the title compound (0.12 g, yield 99%).

Workup

  1. concentrationThe reaction solution was concentrated
  2. customThen, the residue was purified with silica gel column chromatography (hexane:ethyl acetate=2:1)
  3. customcrystallized from diisopropyl ether

Sources & evidence

ORD record
ord-f6678ab964da4a7b81863be96166917f
Source dataset
uspto-grants-2010_09
Patent number
US07795267B2

Reaction notes

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