2,4-Difluorophenyl isocyanate → HCID 23122061, compound

HRID 1713562Notes

Reaction equation

HRID 1713562 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:18]3[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=3)[CH:12]3[CH2:13][NH:14][CH2:15][CH2:16][N:11]3[C:10](=[O:17])[O:9]2)=[CH:4][CH:3]=1.[F:25][C:26]1[CH:31]=[C:30]([F:32])[CH:29]=[CH:28][C:27]=1[N:33]=[C:34]=[O:35]>O1CCCC1.O>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([C:18]3[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=3)[CH:12]3[CH2:13][N:14]([C:34]([NH:33][C:27]4[CH:28]=[CH:29][C:30]([F:32])=[CH:31][C:26]=4[F:25])=[O:35])[CH2:15][CH2:16][N:11]3[C:10](=[O:17])[O:9]2)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 5932582,4-Difluorophenyl isocyanateHCID 23122042HCID 23122042, compound

Product 1

HCID 23122061HCID 23122061, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 1,1-bis(4-methylphenyl)-hexahydro-3H-oxazolo[3,4-a]pyrazin-3-one (0.20 g, 0.62 mmol) in tetrahydrofuran (6 mL) was added 2,4-difluorophenyl isocyanate (0.090 mL, 0.76 mmol) at 0° C., and the mixture was stirred at 0° C. for 1 hour. The reaction solution was diluted with water and then extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and dried over magnesium sulfate. The solid was filtered off, and the filtrate was concentrated. The residue was purified with silica gel column chromatography (hexane:ethyl acetate=98:2 to hexane:ethyl acetate=1:1), and then recrystallized from diisopropyl ether to obtain the title compound (0.20 g, yield 68%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water and saturated brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationThe solid was filtered off
  5. concentrationthe filtrate was concentrated
  6. customThe residue was purified with silica gel column chromatography (hexane:ethyl acetate=98:2 to hexane:ethyl acetate=1:1)
  7. customrecrystallized from diisopropyl ether

Sources & evidence

ORD record
ord-0364540822734329b1c02524419d946f
Source dataset
uspto-grants-2010_09
Patent number
US07795267B2

Reaction notes

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