Triethylamine → N-(2,4-Dichlorophenyl)-3-(phenylmethoxy)benzeneacetamide

HRID 2304683Notes

Reaction equation

HRID 2304683 reaction equation
[Cl:1][C:2]1[CH:8]=[C:7]([Cl:9])[CH:6]=[CH:5][C:3]=1[NH2:4].[C:10]1([CH2:16][O:17][C:18]2[CH:19]=[C:20]([CH2:24][C:25](Cl)=[O:26])[CH:21]=[CH:22][CH:23]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(N(CC)CC)C.C(=O)(O)[O-].[Na+]>ClCCl>[Cl:1][C:2]1[CH:8]=[C:7]([Cl:9])[CH:6]=[CH:5][C:3]=1[NH:4][C:25](=[O:26])[CH2:24][C:20]1[CH:21]=[CH:22][CH:23]=[C:18]([O:17][CH2:16][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:19]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 111232,4-DichloroanilineHCID 516892Sodium BicarbonateHCID 118178352-[3-(Phenylmethoxy)phenyl]acetyl Chloride

Product 1

HCID 23440745N-(2,4-Dichlorophenyl)-3-(phenylmethoxy)benzeneacetamideYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2,4-dichloroaniline (2.67 g, 0.0165 mol) in dichloromethane (20 ml) was slowly added a solution of 2-[3-(phenylmethoxy)phenyl]acetyl chloride (3.84 g, 0.015 mol) in dichloromethane (10 ml). After stirring for three hours, triethylamine (2 ml, 0.015 mol) was added to the reaction and the reaction was allowed to stir overnight. To the reaction was added an aqueous solution of sodium bicarbonate. The mixture was extracted with dichloromethane. The organic layer was washed with brine, dried over MgSO4, filtered and concentrated. The solid was triturated with ether and hexane, then filtered to provide the title compound (4.0 g, 70% yield): ES-MS (m/z) 372 [M+H]+.

Workup

  1. stirringto stir overnight
  2. extractionThe mixture was extracted with dichloromethane
  3. washThe organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe solid was triturated with ether and hexane
  8. filtrationfiltered

Sources & evidence

ORD record
ord-7a48e4680e2e4768815ae7c6abb4b589
Source dataset
uspto-grants-2002_08
Patent number
US06436923B1

Reaction notes

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