Phenylhydrazine → HCID 68423128, compound

HRID 1713520Notes

Reaction equation

HRID 1713520 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(N(C(C)C)CC)(C)C.ClC(O[C:37](=[O:43])OC(Cl)(Cl)Cl)(Cl)Cl.[C:44]1([NH:50][NH2:51])[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1>O1CCCC1.O>[C:44]1([NH:50][NH:51][C:37]([N:13]2[CH2:14][CH2:15][N:10]3[C:9](=[O:16])[O:8][C:7]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)([C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=4)[CH:11]3[CH2:12]2)=[O:43])[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1

Participants

7

Reactant 4

HCID 7516PhenylhydrazineHCID 81531DiisopropylethylamineHCID 94429TriphosgeneHCID 231218811,1-Diphenyltetrahydro-1H-oxazolo[3,4-a]pyrazin-3(5H)-one

Product 1

HCID 68423128HCID 68423128, compoundYield 30.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of hexahydro-1,1-diphenyl-3H-oxazolo[3,4-a]pyrazin-3-one (0.10 g, 0.34 mmol) in tetrahydrofuran (1 mL) were sequentially added diisopropylethylamine (0.15 mL) and bis(trichloromethyl)carbonate (0.10 g, 0.34 mmol), and the mixture was stirred at room temperature for 45 minutes. Next, phenylhydrazine (39 mg, 0.36 mmol) was added thereto, and the mixture was stirred at room temperature for 3 hours. To the reaction solution was added water, and the mixture was extracted with ethyl acetate. The extract was washed with water and concentrated under reduced pressure. The residue was purified with silica gel column chromatography (hexane:ethyl acetate=1:1) and crystallized from ethyl acetate-diisopropyl ether to obtain the title compound (44 mg, yield 30%).

Workup

  1. stirringthe mixture was stirred at room temperature for 3 hours
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with water
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified with silica gel column chromatography (hexane:ethyl acetate=1:1)
  6. customcrystallized from ethyl acetate-diisopropyl ether

Sources & evidence

ORD record
ord-1b601ca10b174dda873c557dca1f8328
Source dataset
uspto-grants-2010_09
Patent number
US07795267B2

Reaction notes

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