Triethylamine → HCID 67537435, compound

HRID 660068Notes

Reaction equation

HRID 660068 reaction equation
[NH2:1][C:2]1[CH:6]=[CH:5][O:4][N:3]=1.C(N(CC)CC)C.[Br:14][CH:15]([CH3:19])[C:16](Br)=[O:17]>C(Cl)(Cl)Cl>[Br:14][CH:15]([CH3:19])[C:16]([NH:1][C:2]1[CH:6]=[CH:5][O:4][N:3]=1)=[O:17]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 79047Propanoyl bromide, 2-bromo-HCID 18102163-Isoxazolamine

Product 1

HCID 67537435HCID 67537435, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Conditions

Temperature
-40 °C

Procedure

To a cooled (−40° C.) stirring solution of 3-aminoisoxazole (0.88 ml, 11.9 mmol) and triethylamine (1.99 ml, 14.3 mmol) in chloroform (6 ml) is added slowly, 2-bromopropionyl bromide (1.37 ml, 13.1 mmol) in chloroform (6 ml). The reaction mixture is stirred at −40° C. for 30 minutes, and then allowed to warm to room temperature. The mixture is then partitioned between 1M aqueous hydrochloric acid and ethyl acetate. The organic extract is washed with saturated sodium hydrogen carbonate, dried over Na2SO4 and the solvent removed in vacuo to afford the titled compound as a yellow oil.

Workup

  1. additionis added slowly
  2. temperatureto warm to room temperature
  3. customThe mixture is then partitioned between 1M aqueous hydrochloric acid and ethyl acetate
  4. extractionThe organic extract
  5. washis washed with saturated sodium hydrogen carbonate
  6. dry with materialdried over Na2SO4
  7. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-9c811392d044423ca551474f05435a6f
Source dataset
uspto-grants-2011_12
Patent number
US08084463B2

Reaction notes

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