Potassium Carbonate → HCID 20553518, compound

HRID 1446884Notes

Reaction equation

HRID 1446884 reaction equation
[CH3:1][N:2]([C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=1)[C:3]1[O:4][C:5]2[CH:11]=[CH:10][C:9]([C:12]([F:15])([F:14])[F:13])=[CH:8][C:6]=2[N:7]=1.Br[CH:24]([CH3:30])[C:25]([O:27][CH2:28][CH3:29])=[O:26].C(=O)([O-])[O-].[K+].[K+]>C(C(C)=O)C>[CH3:1][N:2]([C:16]1[CH:21]=[CH:20][C:19]([O:22][CH:24]([CH3:30])[C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:18][CH:17]=1)[C:3]1[O:4][C:5]2[CH:11]=[CH:10][C:9]([C:12]([F:13])([F:15])[F:14])=[CH:8][C:6]=2[N:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 79040Ethyl 2-bromopropionate2×HCID 20553514HCID 20553514, compound

Product 1

HCID 20553518HCID 20553518, compoundYield 32.7%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 4-[N-methyl-N-(5-trifluoromethyl-2-benzoxazolyl)amino]phenol (1.8 g, 0.006 mole), ethyl 2-bromopropionate (1.2 g, 0.006 mole), ethyl 2-bromopropionate (1.2 g, 0.006 mole), anhydrous potassium carbonate (0.9 g, 0.006 mole) and methyl ethyl ketone (25 ml) was heated under reflux, with stirring, for a period of 7 hours and then allowed to stand at room temperature for a period of 48 hours. The solvent was removed by distillation under reduced pressure and the residue was triturated with a mixture of water and diethyl ether. The combined ethereal extracts (200 ml) were washed with brine, dried over anhydrous magnesium sulfate and the ether evaporated to give a yellow oil. The oil was chromatographed over silica gel (eluant diethyl ether) to give the title compound as a yellow oil (0.8 g).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux
  3. waitto stand at room temperature for a period of 48 hours
  4. customThe solvent was removed by distillation under reduced pressure
  5. customthe residue was triturated with a mixture of water and diethyl ether
  6. washwere washed with brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customthe ether evaporated
  9. customto give a yellow oil
  10. customThe oil was chromatographed over silica gel (eluant diethyl ether)

Sources & evidence

ORD record
ord-54ed640d9a9c454c91f6f008e4beb9b2
Source dataset
uspto-grants-1982_02
Patent number
US04314065

Reaction notes

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