Sodium Carbonate → HCID 14277791, compound

HRID 230994Notes

Reaction equation

HRID 230994 reaction equation
[CH2:1]([N:5]1[C:10]([CH2:11][CH3:12])=[CH:9][C:8](=[O:13])[C:7]([C:14]([NH:16][C:17]2[C:22]([CH2:23][CH3:24])=[CH:21][CH:20]=[CH:19][C:18]=2[CH2:25][CH3:26])=[O:15])=[C:6]1[CH3:27])[CH2:2][CH2:3][CH3:4].C(=O)([O-])[O-].[Na+].[Na+].[Br:34]Br>C(Cl)Cl>[Br:34][C:9]1[C:8](=[O:13])[C:7]([C:14]([NH:16][C:17]2[C:18]([CH2:25][CH3:26])=[CH:19][CH:20]=[CH:21][C:22]=2[CH2:23][CH3:24])=[O:15])=[C:6]([CH3:27])[N:5]([CH2:1][CH2:2][CH2:3][CH3:4])[C:10]=1[CH2:11][CH3:12]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 24408BromineHCID 14151557HCID 14151557, compound

Product 1

HCID 14277791HCID 14277791, compoundYield 72.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of 700 mg (1.90 mmol) of 1-butyl-6-ethyl-N-(2,6-diethylphenyl)-1,4-dihydro-2-methyl-4-oxo-3-pyridinecarboxamide, 14 ml of methylene chloride and 1.2 g (7.40 mmol) of sodium carbonate was added a solution of 303 mg (1.90 mmol) of bromine in 5 ml of methylene chloride under vigorous stirring. After the completion of addition the mixture was stirred for 6 hours. The insoluble product in methylene chloride was filtered off and the filtrate was concentrated in vacuo to give a crystalline residue. The residue was recrystallized from benzene and cyclohexane to afford 615 mg of the title compound having mp. 132.5°-133.5° C.

Workup

  1. additionAfter the completion of addition the mixture
  2. filtrationThe insoluble product in methylene chloride was filtered off
  3. concentrationthe filtrate was concentrated in vacuo
  4. customto give a crystalline residue
  5. customThe residue was recrystallized from benzene and cyclohexane

Sources & evidence

ORD record
ord-8d092b9140fc443584b131c694abfcfe
Source dataset
uspto-grants-1989_07
Patent number
US04844732

Reaction notes

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