N-bromobutanimide → HCID 13822033, compound

HRID 867946Notes

Reaction equation

HRID 867946 reaction equation
[CH2:1]([N:5]1[C:10]([CH3:11])=[CH:9][C:8](=[O:12])[C:7]([C:13]([NH:15][C:16]2[C:21]([CH2:22][CH3:23])=[CH:20][CH:19]=[CH:18][C:17]=2[CH2:24][CH3:25])=[O:14])=[C:6]1[CH3:26])[CH2:2][CH2:3][CH3:4].[Br:27]N1C(=O)CCC1=O>ClCCl>[Br:27][C:9]1[C:8](=[O:12])[C:7]([C:13]([NH:15][C:16]2[C:17]([CH2:24][CH3:25])=[CH:18][CH:19]=[CH:20][C:21]=2[CH2:22][CH3:23])=[O:14])=[C:6]([CH3:26])[N:5]([CH2:1][CH2:2][CH2:3][CH3:4])[C:10]=1[CH3:11]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 13745359HCID 13745359, compound

Product 1

HCID 13822033HCID 13822033, compoundYield 61.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3.0 g (8.5 mmol, m.p. 110°-112° C.) of 1-butyl-N-(2,6-diethylphenyl)-1,4-dihydro-2,6-dimethyl-4-oxo-3-pyridinecarboxamide and 1.7 g (9.6 mmol) of N-bromosuccinimide was dissolved in 100 ml of dichloromethane, and the mixture was stirred for a day at room temperature. The reaction mixture, transferred to a separatory funnel, was washed with water, saturated sodium bicarbonate and water. The organic layer was dried and concentrated in a known manner to give a crystalline residue, and the residue was recrystallized from a mixture of ethyl acetate and hexane, affording 2.25 g of the title compound having m.p. 158°-160.5° C.

Workup

  1. customThe reaction mixture, transferred to a separatory funnel
  2. washwas washed with water, saturated sodium bicarbonate and water
  3. customThe organic layer was dried
  4. concentrationconcentrated in a known manner
  5. customto give a crystalline residue
  6. customthe residue was recrystallized from a mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-46b7474ff1c648bc9cb15973c73e3f56
Source dataset
uspto-grants-1988_10
Patent number
US04777256

Reaction notes

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