Ammonium Chloride → N-(2-Phenoxyphenyl)-N-{[2-(prop-1-en-1-yl)phenyl]methyl}acetamide

HRID 1016583Notes

Reaction equation

HRID 1016583 reaction equation
[CH2:1]([Li])[CH2:2]CC.CCCCCC.[C:12]([N:15]([CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[CH:36]=O)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[O:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)(=[O:14])[CH3:13].[Cl-].[NH4+]>[Br-].C([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)C.O1CCCC1>[C:12]([N:15]([CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[CH:36]=[CH:1][CH3:2])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[O:22][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)(=[O:14])[CH3:13]

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 18407199HCID 18407199, compoundHCID 178418244HCID 178418244, compound

Product 1

HCID 70134079N-(2-Phenoxyphenyl)-N-{[2-(prop-1-en-1-yl)phenyl]methyl}acetamide

Reagents, catalysts & solvents 2

HCID 73727Phosphonium, ethyltriphenyl-, bromide (1:1)CatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of 4.34 g of ethyltriphenyl-phosphonium bromide in 20 ml of tetrahydrofuran was added dropwise 6.63 ml of 1.63 M n-butyl lithium/hexane solution under a nitrogen stream, while keeping the temperature of the reaction solution at −15 to −10° C. The temperature of the reaction solution was gradually raised to room temperature, and after stirring at room temperature for 20 minutes, a solution of 1.01 g of N-acetyl-N-(2-formylbenzyl)-2-phenoxyaniline in 10 ml of tetrahydrofuran was added dropwise, followed by further stirring for an hour. After addition of a saturated aqueous ammonium chloride solution, the reaction solution was extracted with ethyl acetate, and the extract was washed with a saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate. After removal of the drying agent by filtration, the solvent was concentrated under reduced pressure to give 859 mg of N-acetyl-N-[2-(propen-1-yl)benzyl]-2-phenoxyaniline as an oil in a mixture of the geometrical isomers at a ratio of about 3:2.

Workup

  1. customat −15 to −10° C
  2. stirringby further stirring for an hour
  3. extractionthe reaction solution was extracted with ethyl acetate
  4. washthe extract was washed with a saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. customAfter removal of the drying agent
  7. filtrationby filtration
  8. concentrationthe solvent was concentrated under reduced pressure

Sources & evidence

ORD record
ord-5326a53205944c1b86804f14a2e3bcdd
Source dataset
uspto-grants-2002_11
Patent number
US06476056B2

Reaction notes

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