Propargyl bromide → HCID 88608535, compound

HRID 2351290Notes

Reaction equation

HRID 2351290 reaction equation
[CH:1]1[C:13]2[O:12][N:11]=[C:6]3[N:7]=[CH:8][CH2:9][O:10][C:4]([C:5]=23)=[CH:3][CH:2]=1.[H-].[Na+].[CH2:16](Br)[C:17]#[CH:18]>CN(C)C=O>[CH2:18]([C:3]1[CH:2]=[CH:1][C:13]2[O:12][N:11]=[C:6]3[N:7]=[CH:8][CH2:9][O:10][C:4]=1[C:5]=23)[C:17]#[CH:16]

Participants

5

Reactant 3

HCID 7842Propargyl bromideHCID 24758Sodium hydrideHCID 70362693HCID 70362693, compound

Product 1

HCID 88608535HCID 88608535, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 4,5-dihydroisoxazolo[3,4,5-ef][1,4]benzoxazepine of Example 7(b ) (3.9 g; 22.1 mmoles) in 120 ml dimethylformamide was added to a suspension of sodium hydride (1.4 g; 27.7 mmoles). This was followed by a solution of propargyl bromide (2.7 ml of 80% solution; 24.4 mmoles). The reaction was heated at 80° C. for 1.5 hours and then quenched into water (400 ml). The resulting precipitate was filtered, rinsed and dried, then passed through a column of florisil (ethyl acetate/dichloromethane). This gave 3.5 g of a solid, mp 100°-104° C., which was recrystallized from isopropanol to give 2.5 g (53%) of 4,5-dihydro-3-(2-propynyl)isoxazolo[3,4,5-ef][1,4]benzoxazepine, mp 104°-106° C.

Workup

  1. customquenched into water (400 ml)
  2. filtrationThe resulting precipitate was filtered
  3. washrinsed
  4. customdried
  5. customThis gave 3.5 g of a solid, mp 100°-104° C., which was recrystallized from isopropanol

Sources & evidence

ORD record
ord-a6b1a79a004a425b989983d0e9eca23a
Source dataset
uspto-grants-1989_10
Patent number
US04873234

Reaction notes

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