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Dimethylformamide → 2-(3-Chloro-biphenyl-4-yloxy)-n-[3-chloro-4-(2-diethylamino-ethoxy)-phenyl]-acetamide

HRID 898558
Notes
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Reaction equation

HRID 898558 reaction equation
C(=O)([O-])[O-].[K+].[K+].Br.Br[CH2:9][C:10]([NH:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][N:22]([CH2:25][CH3:26])[CH2:23][CH3:24])=[C:15]([Cl:27])[CH:14]=1)=[O:11].[Cl:28][C:29]1[CH:30]=[C:31]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH:32]=[CH:33][C:34]=1[OH:35].CN(C=O)C>ClCCl>[Cl:28][C:29]1[CH:30]=[C:31]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH:32]=[CH:33][C:34]=1[O:35][CH2:9][C:10]([NH:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][N:22]([CH2:25][CH3:26])[CH2:23][CH3:24])=[C:15]([Cl:27])[CH:14]=1)=[O:11]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 70742-Chloro-4-PhenylphenolHCID 11430Potassium CarbonateHCID 688779532-Bromo-n-[3-chloro-4-(2-diethylamino-ethoxy)-phenyl]-acetamide-hydrobromide

Product 1

HCID 103453352-(3-Chloro-biphenyl-4-yloxy)-n-[3-chloro-4-(2-diethylamino-ethoxy)-phenyl]-acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

65 mg (0.47 mmol) of potassium carbonate was added to a solution of 70 mg (0.159 mmol) of 2-bromo-N-[3-chloro-4-(2-diethylamino-ethoxy)-phenyl]-acetamide-hydrobromide (intermediate product Z1c) and 64 mg (0.314 mmol) of 3-chloro-biphenyl-4-ol in 1 mL of abs. DMF and the mixture was stirred for 1 hour at 40° C. and for 15 hours at RT. The reaction mixture was diluted with dichloromethane, the org. phase was washed with sat. aqueous sodium bicarbonate solution and water and dried over magnesium sulphate. Column chromatography (silica gel, dichloromethane/MeOH 9:1) yielded the product.

Workup

  1. washphase was washed with sat. aqueous sodium bicarbonate solution and water
  2. dry with materialdried over magnesium sulphate
  3. customColumn chromatography (silica gel, dichloromethane/MeOH 9:1) yielded the product

Sources & evidence

ORD record
ord-8ca1535cfe144253bdfececabfc75dec
Source dataset
uspto-grants-2008_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07351719B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes