4-Fluorophenyl isocyanate → HCID 23121923, compound

HRID 1713525Notes

Reaction equation

HRID 1713525 reaction equation
[CH3:1][C:2]1([CH3:12])[CH:6]2[CH2:7][NH:8][CH2:9][CH2:10][N:5]2[C:4](=[O:11])[O:3]1.[F:13][C:14]1[CH:19]=[CH:18][C:17]([N:20]=[C:21]=[O:22])=[CH:16][CH:15]=1>O1CCCC1>[F:13][C:14]1[CH:19]=[CH:18][C:17]([NH:20][C:21]([N:8]2[CH2:9][CH2:10][N:5]3[C:4](=[O:11])[O:3][C:2]([CH3:12])([CH3:1])[CH:6]3[CH2:7]2)=[O:22])=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 709554-Fluorophenyl isocyanateHCID 231220551,1-Dimethylhexahydro-3H-[1,3]oxazolo[3,4-a]pyrazin-3-one

Product 1

HCID 23121923HCID 23121923, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

Hexahydro-1,1-dimethyl-3H-oxazolo[3,4-a]pyrazin-3-one (0.10 g, 0.59 mmol) was dissolved in tetrahydrofuran (10 mL). 4-Fluorophenyl isocyanate (0.12 g, 0.88 mmol) was added thereto, and the mixture was stirred at 50° C. for 4 hours. The reaction solution was concentrated under reduced pressure. The residue was purified with silica gel column chromatography (hexane:ethyl acetate=1:1 to 1:9). After purification, the crystals, which were precipitated while concentrating under reduced pressure, were collected by filtration to obtain the title compound (136 mg, yield 75%).

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. customThe residue was purified with silica gel column chromatography (hexane:ethyl acetate=1:1 to 1:9)
  3. customAfter purification
  4. customthe crystals, which were precipitated
  5. concentrationwhile concentrating under reduced pressure
  6. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-5a3ab73214614c15a143946eb0cbe1d2
Source dataset
uspto-grants-2010_09
Patent number
US07795267B2

Reaction notes

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