2-(m-Aminophenoxy)-myristic acid ethyl ester → 2-[m-(3-Chloro-2,2,3-trifluoropropionamido)-phenoxy]-myristic acid ethyl ester

HRID 620699Notes

Reaction equation

HRID 620699 reaction equation
[Cl:1][CH:2]([F:9])[C:3]([F:8])([F:7])[C:4](Cl)=[O:5].[CH2:10]([O:12][C:13](=[O:35])[CH:14]([O:27][C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([NH2:34])[CH:29]=1)[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH3:11]>ClCCl.N1C=CC=CC=1>[CH2:10]([O:12][C:13](=[O:35])[CH:14]([O:27][C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([NH:34][C:4](=[O:5])[C:3]([F:8])([F:7])[CH:2]([Cl:1])[F:9])[CH:29]=1)[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH3:11]

Participants

5

Reactant 2

HCID 141224152-(m-Aminophenoxy)-myristic acid ethyl esterHCID 141224163-Chloro-2,2,3-trifluoro-propionyl chloride

Product 1

HCID 141224172-[m-(3-Chloro-2,2,3-trifluoropropionamido)-phenoxy]-myristic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

An amount of 63.35 g (0.35 mol) of 3-chloro-2,2,3-trifluoro-propionyl chloride is added dropwise in 30 min to a solution of 109 g (0.3 mol) of 2-(m-aminophenoxy)-myristic acid ethyl ester in 450 ml of dichloromethane and 48 ml of pyridine. A slight reflux is observed. The mixture is then refluxed for 2 h. Subsequently, the reaction mixture is washed first with 1N hydrochloric acid and next with water until neutral. The solvent is removed by evaporation.

Workup

  1. temperatureA slight reflux
  2. temperatureThe mixture is then refluxed for 2 h
  3. washSubsequently, the reaction mixture is washed first with 1N hydrochloric acid and next with water until neutral
  4. customThe solvent is removed by evaporation

Sources & evidence

ORD record
ord-a64936ff43c64059913b8a7831e9fd1b
Source dataset
uspto-grants-1989_04
Patent number
US04822729

Reaction notes

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