Acetic Acid → HCID 18407188, compound

HRID 2271198Notes

Reaction equation

HRID 2271198 reaction equation
[C:1]([OH:4])(=O)C.[CH2:5]([N:7](CC)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.[CH3:29][O:30][C:31]1[CH:51]=[CH:50][C:49]([O:52][CH3:53])=[CH:48][C:32]=1[CH2:33][NH:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=1[O:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1>C1C=CC=CC=1.O>[CH3:29][O:30][C:31]1[CH:51]=[CH:50][C:49]([O:52][CH3:53])=[CH:48][C:32]=1[CH2:33][N:34]([C:1]([NH:7][CH3:5])=[O:4])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=1[O:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 18407200HCID 18407200, compound

Product 1

HCID 18407188HCID 18407188, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

To a solution of 3.43 ml of acetic acid and 8.36 ml of triethylamine in 90 ml of benzene was added 12.9 ml of diphenylphosphoryl azide, followed by reflux under heating for 2 hours. To the reaction solution was added 2.01 g of N-(2,5-dimethoxybenzyl)-2-phenoxyaniline synthesized in the same manner as in Example 2(1), followed by reflux under heating for 6 hours. The reaction mixture was poured into water, and the organic phase was separated, washed with 5% hydrochloric acid, a saturated aqueous sodium bicarbonate solution and a saturated aqueous sodium chloride solution, successively, and dried over anhydrous sodium sulfate. After removal of the drying agent by filtration, the solvent was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent; ethyl acetate-hexane=1:2) and recrystallized from diethyl ether to give 1.20 g of N-(2,5-dimethoxybenzyl)-N-(N-methylaminocarbonyl)-2-phenoxyaniline.

Workup

  1. temperatureby reflux
  2. temperatureunder heating for 2 hours
  3. customsynthesized in the same manner as in Example 2(1)
  4. temperatureby reflux
  5. temperatureunder heating for 6 hours
  6. customthe organic phase was separated
  7. washwashed with 5% hydrochloric acid
  8. dry with materiala saturated aqueous sodium bicarbonate solution and a saturated aqueous sodium chloride solution, successively, and dried over anhydrous sodium sulfate
  9. customAfter removal of the drying agent
  10. filtrationby filtration
  11. concentrationthe solvent was concentrated under reduced pressure
  12. customthe residue was purified by silica gel column chromatography (eluent; ethyl acetate-hexane=1:2)
  13. customrecrystallized from diethyl ether

Sources & evidence

ORD record
ord-e58278094f0848ceada59abcce774e2d
Source dataset
uspto-grants-2001_12
Patent number
US06333358B1

Reaction notes

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