Water → HCID 18407217, compound

HRID 2271196Notes

Reaction equation

HRID 2271196 reaction equation
[CH3:1][O:2][C:3]1[CH:23]=[CH:22][CH:21]=[CH:20][C:4]=1[CH2:5][NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[O-:24][C:25]#[N:26].[K+].O>C(O)(=O)C>[NH2:26][C:25]([N:6]([CH2:5][C:4]1[CH:20]=[CH:21][CH:22]=[CH:23][C:3]=1[O:2][CH3:1])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[O:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)=[O:24]

Participants

5

Reactant 3

HCID 962WaterHCID 11378442Potassium cyanateHCID 18407190HCID 18407190, compound

Product 1

HCID 18407217HCID 18407217, compoundYield 96.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

In 20 ml of acetic acid was dissolved 1.54 g of N-(2-methoxybenzyl)-2-phenoxyaniline synthesized in the same manner as in Example 1(1), and then an aqueous potassium cyanate solution (1.23 g of potassium cyanate and 10 ml of water) was added dropwise to the solution, followed by stirring at room temperature for 2.5 hours. The reaction mixture was poured into water and extracted with ethyl acetate, and the extract was washed with a saturated aqueous sodium bicarbonate solution and a saturated sodium chloride solution 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=1:3) to give 1.69 g of N-aminocarbonyl-N-(2-methoxybenzyl)-2-phenoxyaniline as an oil.

Workup

  1. customsynthesized in the same manner as in Example 1(1)
  2. extractionextracted with ethyl acetate
  3. washthe extract was washed with a saturated aqueous sodium bicarbonate solution
  4. dry with materiala saturated sodium chloride solution and dried over anhydrous sodium sulfate
  5. customAfter removal of the drying agent
  6. filtrationby filtration
  7. concentrationthe solvent was concentrated under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (eluent; ethyl acetate-hexane=1:3)

Sources & evidence

ORD record
ord-261e97ea211945448068dc4630f9bf38
Source dataset
uspto-grants-2001_12
Patent number
US06333358B1

Reaction notes

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