N-bromobutanimide → HCID 13654178, compound

HRID 1249445Notes

Reaction equation

HRID 1249445 reaction equation
[CH3:1][C:2]1[N:6]([C:7]([CH3:10])([CH3:9])[CH3:8])[N:5]=[CH:4][C:3]=1[C:11]([O:13][CH2:14][CH3:15])=[O:12].[Br:16]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:16][CH2:1][C:2]1[N:6]([C:7]([CH3:10])([CH3:8])[CH3:9])[N:5]=[CH:4][C:3]=1[C:11]([O:13][CH2:14][CH3:15])=[O:12]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 13654177ethyl 1-tert-butyl-5-methyl-1H-pyrazole-4-carboxylate

Product 1

HCID 13654178HCID 13654178, compoundYield 85.2%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

5-Methyl-1-tert-butyl-1H-pyrazole-4-carboxylic acid, ethyl ester (30 grams, 0.14 mole) and N-bromosuccinimide (25.4 grams, 0.14 mole) were combined in 100 ml. of carbon tetrachloride. A heating lamp was turned onto the reaction mixture, and the reaction mixture was refluxed for three hours. The reaction mixture was then cooled and filtered to remove the succinimide. The filtrate was washed with water, washed with saturated brine, and dried over sodium sulfate and filter paper. The solvent was then removed in vacuo, providing 34.5 grams of the 5-(bromomethyl)-1-tert-butyl-1H-pyrazole-4-carboxylic acid, ethyl ester.

Workup

  1. customA heating lamp was turned onto the reaction mixture
  2. temperaturethe reaction mixture was refluxed for three hours
  3. temperatureThe reaction mixture was then cooled
  4. filtrationfiltered
  5. customto remove the succinimide
  6. washThe filtrate was washed with water
  7. washwashed with saturated brine
  8. dry with materialdried over sodium sulfate
  9. filtrationfilter paper
  10. customThe solvent was then removed in vacuo

Sources & evidence

ORD record
ord-ac07489dff6c4f09ab115e6d20f7281e
Source dataset
uspto-grants-1986_12
Patent number
US04631343

Reaction notes

Loading…