N-bromobutanimide → HCID 15675830, compound

HRID 345095Notes

Reaction equation

HRID 345095 reaction equation
[Br:1]N1C(=O)CCC1=O.[Br:9][C:10]1[CH:11]=[N:12][N:13]2[C:18]3[N:19]([CH2:22][CH3:23])[CH:20]=[CH:21][C:17]=3[C:16]([CH3:24])=[N:15][C:14]=12>C(Cl)(Cl)Cl>[Br:9][C:10]1[CH:11]=[N:12][N:13]2[C:18]3[N:19]([CH2:22][CH3:23])[C:20]([Br:1])=[CH:21][C:17]=3[C:16]([CH3:24])=[N:15][C:14]=12

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 15675820HCID 15675820, compound

Product 1

HCID 15675830HCID 15675830, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

N-bromosuccinimide was added at room temperature to a solution of 1.675 g (6 mmoles) of 3-bromo-8-ethyl-5-methyl-8H-pyrazolo[1,5-a]pyrrolo[3,2-e]pyrimidine (prepared as described in Example 13) dissolved in 12 ml of chloroform, and the mixture was stirred for 2 hours. At the end of this time, the reaction mixture was washed with a 2N aqueous solution of potassium hydroxide and then with water, after which it was dried over anhydrous sodium sulfate and then concentrated by evaporation under reduced pressure. The residue was purified by column chromatography through silica gel (eluted with chloroform) and recrystallized from ethyl acetate to afford 1.72 g (yield 80%) of the title compound as colorless needles, melting at 135°-137° C.

Workup

  1. washAt the end of this time, the reaction mixture was washed with a 2N aqueous solution of potassium hydroxide
  2. dry with materialwith water, after which it was dried over anhydrous sodium sulfate
  3. concentrationconcentrated by evaporation under reduced pressure
  4. customThe residue was purified by column chromatography through silica gel (eluted with chloroform)
  5. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-6260ea440c7a462db3db89268b0cb31c
Source dataset
uspto-grants-1991_10
Patent number
US05055479

Reaction notes

Loading…