Diisopropylethylamine → n-[3-Chloro-4-(2-diethylamino-ethoxy)-phenyl]-3-(2,4-dichloro-phenyl)-propionamide

HRID 898568Notes

Reaction equation

HRID 898568 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH2:9][CH2:10][C:11]([OH:13])=O.[Cl:14][C:15]1[CH:16]=[C:17]([NH2:29])[CH:18]=[CH:19][C:20]=1[O:21][CH2:22][CH2:23][N:24]([CH2:27][CH3:28])[CH2:25][CH3:26].C(N(C(C)C)C(C)C)C>S(Cl)(Cl)=O.ClCCl>[Cl:14][C:15]1[CH:16]=[C:17]([NH:29][C:11](=[O:13])[CH2:10][CH2:9][C:3]2[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=2[Cl:1])[CH:18]=[CH:19][C:20]=1[O:21][CH2:22][CH2:23][N:24]([CH2:27][CH3:28])[CH2:25][CH3:26]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 27409153-(2,4-Dichlorophenyl)propanoic acidHCID 16791676HCID 16791676, compound

Product 1

HCID 59691703n-[3-Chloro-4-(2-diethylamino-ethoxy)-phenyl]-3-(2,4-dichloro-phenyl)-propionamide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 24386Thionyl ChlorideSolvent

Procedure

A solution of 0.271 g (1.236 mmol) of (3-(2,4-dichloro-phenyl)-propionic acid in 3.00 mL thionyl chloride was stirred for 2 hours at RT, evaporated down i. vac. and dissolved in 10 mL dichloromethane. This solution of the acid chloride was slowly added dropwise, while cooling with ice, to a solution of 0.300 (1.236 mmol) of 3-chloro-4-(2-diethylamino-ethoxy)-phenylamine (intermediate product Z1b) and 0.32 mL (1.854 mmol) of ethyl-diisopropylamine in 10 mL dichloromethane and the mixture was stirred for 16 hours at RT. The reaction mixture was washed with sat. aqueous sodium bicarbonate solution, dried over magnesium sulphate and evaporated down i. vac. The residue was dissolved in EtOAc and purified by column chromatography (silica gel, EtOAc/MeOH/conc. aqueous ammonia 90:10:1).

Workup

  1. customevaporated down i
  2. dissolutionand dissolved in 10 mL dichloromethane
  3. additionThis solution of the acid chloride was slowly added dropwise
  4. washThe reaction mixture was washed with sat. aqueous sodium bicarbonate solution
  5. dry with materialdried over magnesium sulphate
  6. customevaporated down i
  7. dissolutionThe residue was dissolved in EtOAc
  8. custompurified by column chromatography (silica gel, EtOAc/MeOH/conc. aqueous ammonia 90:10:1)

Sources & evidence

ORD record
ord-d189a454ed0a4e21986af81d52b7e129
Source dataset
uspto-grants-2008_04
Patent number
US07351719B2

Reaction notes

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