Ketone, 2,4-dimethylpyrrol-3-yl methyl → HCID 4319583, compound

HRID 2228614Notes

Reaction equation

HRID 2228614 reaction equation
[C:1]([C:4]1[C:8]([CH3:9])=[CH:7][NH:6][C:5]=1[CH3:10])(=[O:3])[CH3:2].C1C(=O)N([Br:18])C(=O)C1.S([O-])([O-])=O.[Na+].[Na+]>C1COCC1>[C:1]([C:4]1[C:8]([CH3:9])=[C:7]([Br:18])[NH:6][C:5]=1[CH3:10])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 15163Ketone, 2,4-dimethylpyrrol-3-yl methylHCID 24437Sodium SulfiteHCID 67184N-bromobutanimide

Product 1

HCID 4319583HCID 4319583, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred suspension of 3-acetyl-2,4-dimethyl-1H-pyrrole (2.89 g, 21.1 mmol) in THF (80 mL) was added NBS (3.75 g, 21.1 mmol) at −78° C. under nitrogen. After stirring for 30 minutes at same temperature, the mixture was allowed to warm to room temperature and stirred for 1 hour. Sodium sulfite (4.3 g) was added to the mixture and volatiles were removed by evaporation. Water (100 mL) was added to the mixture, and the precipitates were collected by filtration to give 5.33 g (quant. including water) of the subtitle product.

Workup

  1. stirringstirred for 1 hour
  2. customwere removed by evaporation
  3. additionWater (100 mL) was added to the mixture
  4. filtrationthe precipitates were collected by filtration

Sources & evidence

ORD record
ord-0c3567dbca57447a8985edf4baa935fc
Source dataset
uspto-grants-2002_07
Patent number
US06417202B1

Reaction notes

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