Potassium Carbonate → HCID 20522427, compound

HRID 223422Notes

Reaction equation

HRID 223422 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[OH:9].Br[CH:11]([CH3:17])[C:12]([N:14]([CH3:16])[CH3:15])=[O:13].C(=O)([O-])[O-].[K+].[K+]>C(C(C)=O)C(C)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[O:9][CH:11]([CH3:17])[C:12]([N:14]([CH3:16])[CH3:15])=[O:13]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 113673482-BROMO-N,N-DIMETHYLPROPANAMIDEHCID 132842722-Bromo-5-chlorophenol

Product 1

HCID 20522427HCID 20522427, compound

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

2-Bromo-5-chlorophenol (8 g), 2-bromo-N,N-dimethylpropionamide (6.66 g) and anhydrous potassium carbonate (2.6 g) in methyl iso-butyl ketone (100 ml) were refluxed with stirring overnight. The mixture was cooled to 50° and washed with 5% sodium hydroxide (2×20 ml) and then water (2×50 ml). The organic solution was dried and evaporated under reduced pressure to yield a pale red oil, which solidified on cooling. Recrystallisation from 50% aqueous ethanol gave the title compound, m.p. 76°-77°. Compounds 2, 9, 10 to 13, 17 and 21 were made by a similar procedure.

Workup

  1. temperatureThe mixture was cooled to 50°
  2. washwashed with 5% sodium hydroxide (2×20 ml)
  3. customThe organic solution was dried
  4. customevaporated under reduced pressure
  5. customto yield a pale red oil, which
  6. temperatureon cooling
  7. customRecrystallisation from 50% aqueous ethanol

Sources & evidence

ORD record
ord-ad3a008e04e24562b6d7371dc02fdf10
Source dataset
uspto-grants-1982_10
Patent number
US04354034

Reaction notes

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