Phosphorus oxychloride → HCID 18696149, compound

HRID 1739056Notes

Reaction equation

HRID 1739056 reaction equation
C(OC([NH:8][CH2:9][CH2:10][O:11][C:12]1[C:16]2[C:17]([C:22](=O)[NH2:23])=[C:18]([F:21])[CH:19]=[CH:20][C:15]=2[O:14][N:13]=1)=O)(C)(C)C.P(Cl)(Cl)([Cl:27])=O>CN(C)C=O>[ClH:27].[NH2:8][CH2:9][CH2:10][O:11][C:12]1[C:16]2[C:17]([C:22]#[N:23])=[C:18]([F:21])[CH:19]=[CH:20][C:15]=2[O:14][N:13]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 15453960HCID 15453960, compound

Product 1

HCID 18696149HCID 18696149, compoundYield 105.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
5 °C

Procedure

To a solution of 3-(2-(N-t-butoxycarbonylamino)ethoxy)-4-carbamoyl-5-fluoro-1,2-benzisoxazole (0.25 g) in dimethylformamide (2.0 ml) was added phosphorus oxychloride (0.12 g) with stirring at 5° C., and the mixture was then stirred at the same temperature for 15 minutes. The reaction mixture was poured into ice water (20 ml), extracted with ethyl acetate (twice each with 20 ml) and the combined extracts were dried over anhydrous magnesium sulphate and filtered. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography with cyclohexane/ethyl acetate (4/1) as an eluent, to give the title compound (0.20 g, 87% yield) as a colorless powder.

Workup

  1. stirringthe mixture was then stirred at the same temperature for 15 minutes
  2. extractionextracted with ethyl acetate (twice each with 20 ml) and the combined extracts
  3. dry with materialwere dried over anhydrous magnesium sulphate
  4. filtrationfiltered
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography with cyclohexane/ethyl acetate (4/1) as an eluent

Sources & evidence

ORD record
ord-7428af6012034bdc9e2bd1296435980d
Source dataset
uspto-grants-1999_10
Patent number
US05965591

Reaction notes

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