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Hydroxyphenylacetic acid → N-(3,4-Dichlorophenyl)-2-(4-hydroxyphenyl)-N-(2-[3-(phenylmethoxy)phenyl]ethyl}acetamide

HRID 2114723
Notes
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Reaction equation

HRID 2114723 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:13]=2)[CH:5]=[CH:6][C:7]=1[Cl:8].[OH:26][C:27]1[CH:32]=[CH:31][C:30]([CH2:33][C:34](O)=[O:35])=[CH:29][CH:28]=1.P(Cl)(Cl)Cl>ClC1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([N:9]([CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH2:19][C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH:13]=2)[C:34](=[O:35])[CH2:33][C:30]2[CH:31]=[CH:32][C:27]([OH:26])=[CH:28][CH:29]=2)[CH:5]=[CH:6][C:7]=1[Cl:8]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 127Hydroxyphenylacetic acidHCID 24387Phosphorus trichlorideHCID 23440874HCID 23440874, compound

Product 1

HCID 23440903N-(3,4-Dichlorophenyl)-2-(4-hydroxyphenyl)-N-(2-[3-(phenylmethoxy)phenyl]ethyl}acetamideYield 99%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Conditions

Temperature
135 °C

Procedure

To a solution of (3,4-dichlorophenyl) {2-[3-(phenylmethoxy)phenyl]ethyl}amine (4.32 g, 0.011 mol) in chlorobenzene (40 ml) was added 4-hydroxy phenyl acetic acid (2.43 g, 0.014 mol), followed by phosphorus trichloride (5 ml, 0.005 mol). The reaction was allowed to reflux at 135° C. overnight. Solvent was removed and the reaction was basified with 10% sodium hydroxide solution. The reaction was diluted with ethyl acetate and water. The organic was washed with brine, dried with MgSO4, filtered, and concentrated to provide the title compound (5.5 g, 99% yield): ES-MS (m/z) 506 [M+H]+.

Workup

  1. customSolvent was removed
  2. additionThe reaction was diluted with ethyl acetate and water
  3. washThe organic was washed with brine
  4. dry with materialdried with MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-aaf5a59170f844fd85627a14cf8b1ae2
Source dataset
uspto-grants-2008_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07435729B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes