Phosphorus oxychloride → HCID 18696231, compound

HRID 1739059Notes

Reaction equation

HRID 1739059 reaction equation
C(OC([NH:8][CH2:9][CH2:10][O:11][C:12]1[C:16]2[C:17]([C:21](=O)[NH2:22])=[CH:18][CH:19]=[CH:20][C:15]=2[O:14][N:13]=1)=O)(C)(C)C.P(Cl)(Cl)([Cl:26])=O>C(N(CC)C=O)C>[ClH:26].[NH2:8][CH2:9][CH2:10][O:11][C:12]1[C:16]2[C:17]([C:21]#[N:22])=[CH:18][CH:19]=[CH:20][C:15]=2[O:14][N:13]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 18696151HCID 18696151, compound

Product 1

HCID 18696231HCID 18696231, compoundYield 116.2%

Reagents, catalysts & solvents 1

HCID 12051DiethylformamideSolvent

Conditions

Temperature
5 °C

Procedure

To a solution of 3-(2-(N-t-butoxycarbonylamino)ethoxy)-4-carbamoyl-1,2-benzisoxazole (0.15 g) in diethylformamide (1.5 ml) was added phosphorus oxychloride (0.09 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. After filtration, 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 (0.13 g, 93%) 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. filtrationAfter filtration
  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-145eabb2957c42f08252f5002950184d
Source dataset
uspto-grants-1999_10
Patent number
US05965591

Reaction notes

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