2-Nitro-4-(trifluoromethyl)phenol → Ethyl 4-{4-[N-methyl-N-(5-chloro-2-benzoxazolyl)amino]phenoxy}valerate

HRID 1446885Notes

Reaction equation

HRID 1446885 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.[N+](C1C=C(C(F)(F)F)C=CC=1O)([O-])=O.Br[CH:35]([CH3:43])[CH2:36][CH2:37][C:38]([O:40][CH2:41][CH3:42])=[O:39].C(=O)([O-])[O-].[K+].[K+]>C(C(C)=O)C(C)C>[CH3:1][N:2]([C:13]1[CH:18]=[CH:17][C:16]([O:19][CH:35]([CH3:43])[CH2:36][CH2:37][C:38]([O:40][CH2:41][CH3:42])=[O:39])=[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

6

Reactant 4

HCID 98162-Nitro-4-(trifluoromethyl)phenolHCID 11430Potassium Carbonate2×HCID 316888Ethyl 4-bromopentanoateHCID 133148194-[N-Methyl-N-(5-chloro-2-benzoxazolyl)amino]phenol

Product 1

HCID 20553513Ethyl 4-{4-[N-methyl-N-(5-chloro-2-benzoxazolyl)amino]phenoxy}valerate

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A mixture of 4-[N-methyl-N-(5-chloro-2-benzoxazolyl)amino]phenol (1.0 g, 0.0039 mole; see Example 7 part (a), ethyl 4-bromovalerate (0.89 g, 0.0043 mole), anhydrous potassium carbonate (0.54 g) and methyl isobutyl ketone (15 ml) was heated under reflux for a period of 30 hours with further portions (0.05 g) of anhydrous potassium carbonate being added at 3 hour intervals. The reaction mixture was cooled, filtered and the filtrate was distilled under reduced pressure to remove the solvent. The residue (a red oil) was distilled under reduced pressure, bp 240°-260° C. at 0.04 mm Hg and the distillate was further purified by preparative thin layer chromatography on silica gel (eluent chloroform/ethanol 15:1) to give the title compound (0.47 g) as a red oil. The pmr and mass spectra of the compound were consistent with the assigned structure.

Workup

  1. temperaturewas heated
  2. additionadded at 3 hour intervals
  3. temperatureThe reaction mixture was cooled
  4. filtrationfiltered
  5. distillationthe filtrate was distilled under reduced pressure
  6. customto remove the solvent
  7. distillationThe residue (a red oil) was distilled under reduced pressure, bp 240°-260° C. at 0.04 mm Hg
  8. distillationthe distillate was further purified by preparative thin layer chromatography on silica gel (eluent chloroform/ethanol 15:1)

Sources & evidence

ORD record
ord-a200b90e715b4c81ba9c6dfa42650979
Source dataset
uspto-grants-1982_02
Patent number
US04314065

Reaction notes

Loading…