Sodium hydride → HCID 14371417, compound

HRID 2291982Notes

Reaction equation

HRID 2291982 reaction equation
[C:1]1([C:7]([C:10]2[C:14]([NH:15][C:16](=[O:19])[CH2:17]Cl)=[C:13]([CH3:20])[O:12][N:11]=2)([OH:9])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+]>O1CCCC1>[CH3:20][C:13]1[O:12][N:11]=[C:10]2[C:7]([CH3:8])([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[O:9][CH2:17][C:16](=[O:19])[NH:15][C:14]=12

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 14371416HCID 14371416, compound

Product 1

HCID 14371417HCID 14371417, compoundYield 51.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 7.25 g of N-[3-(1-phenyl-1-hydroxyethyl)-5-methylisoxazol-4-yl]chloroacetamide in 36 ml of tetrahydrofuran was added, dropwise under nitrogen, to a suspension of sodium hydride, from washing 2.5 g of a 50% (by weight) oil suspension with hexane, in 146 ml of tetrahydrofuran. The resulting mixture was refluxed for two hours, concentrated, and quenched with 250 ml of ice water. The resulting precipitate was collected, washed with hexane and dried under vacuum (phosphorus pentoxide). Recrystallization from methanol afforded 3.25 g of 4,8-dihydro-3,8-dimethyl-8-phenylisoxazolo[4,3-e][1,4]oxazepin-5(6H)-one, m.p. 177°-178° C.

Workup

  1. washfrom washing 2.5 g of a 50% (by weight) oil suspension with hexane
  2. temperatureThe resulting mixture was refluxed for two hours
  3. concentrationconcentrated
  4. customquenched with 250 ml of ice water
  5. customThe resulting precipitate was collected
  6. washwashed with hexane
  7. dry with materialdried under vacuum (phosphorus pentoxide)
  8. customRecrystallization from methanol

Sources & evidence

ORD record
ord-211a9bda99ac46f890731448dc791bcb
Source dataset
uspto-grants-1989_01
Patent number
US04800200

Reaction notes

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