Potassium Carbonate → Ethyl 2-{4-[N-methyl-N-(5-chloro-2-benzoxazolyl)amino]phenoxy}propionate

HRID 1446875Notes

Reaction equation

HRID 1446875 reaction equation
[CH3:1][N:2]([C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=1)[C:3]1[O:4][C:5]2[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][C:6]=2[N:7]=1.Br[CH:21]([CH3:27])[C:22]([O:24][CH2:25][CH3:26])=[O:23].C(=O)([O-])[O-].[K+].[K+]>C(C(C)=O)C>[CH3:1][N:2]([C:13]1[CH:18]=[CH:17][C:16]([O:19][CH:21]([CH3:27])[C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:15][CH:14]=1)[C:3]1[O:4][C:5]2[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][C:6]=2[N:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 79040Ethyl 2-bromopropionateHCID 133148194-[N-Methyl-N-(5-chloro-2-benzoxazolyl)amino]phenol

Product 1

HCID 13314823Ethyl 2-{4-[N-methyl-N-(5-chloro-2-benzoxazolyl)amino]phenoxy}propionate

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

4-[N-Methyl-N-(5-chloro-2-benzoxazolyl)amino]phenol (0.00255 mol, 0.7 g, prepared as above), ethyl 2-bromopropionate (0.00255 mol, 0.46 g) and potassium carbonate (0.00255 mol, 0.35 g) were mixed in methyl ethyl ketone (5 ml) and heated under reflux for 6 hours. The solvent was then evaporated, the residue taken into water (25 ml) and twice extracted with diethyl ether (25 ml). An oily residue was obtained which was purified by preparative thin layer chromatography on silica gel, eluent toluene/diethyl ether. Yield 0.75 g, mp 68.0°-68.6° C.; ir, and pmr spectra and analysis consistent with assigned structure.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 6 hours
  3. customThe solvent was then evaporated
  4. extractiontwice extracted with diethyl ether (25 ml)
  5. customAn oily residue was obtained which
  6. customwas purified by preparative thin layer chromatography on silica gel, eluent toluene/diethyl ether

Sources & evidence

ORD record
ord-ccd6d813fe9945f8847a0f6dcac28dc2
Source dataset
uspto-grants-1982_02
Patent number
US04314065

Reaction notes

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