N-bromobutanimide → HCID 13654178, compound

HRID 280463Notes

Reaction equation

HRID 280463 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-2017952109b2420b87f681cae1ba2b2c
Source dataset
uspto-grants-1986_05
Patent number
US04589905

Reaction notes

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