(2-Chloro-4-trifluoromethyl-phenoxy)-acetic acid → n-[3-Chloro-4-(2-diethylamino-ethyl)-phenyl]-2-(2-chloro-4-trifluoromethyl-phenoxy)-acetamide

HRID 898632Notes

Reaction equation

HRID 898632 reaction equation
[Cl:1][C:2]1[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:10]=[CH:9][C:3]=1[O:4][CH2:5][C:6]([OH:8])=O.[Cl:17][C:18]1[CH:19]=[C:20]([NH2:31])[CH:21]=[CH:22][C:23]=1[CH2:24][CH2:25][N:26]([CH2:29][CH3:30])[CH2:27][CH3:28]>>[Cl:17][C:18]1[CH:19]=[C:20]([NH:31][C:6](=[O:8])[CH2:5][O:4][C:3]2[CH:9]=[CH:10][C:11]([C:13]([F:16])([F:15])[F:14])=[CH:12][C:2]=2[Cl:1])[CH:21]=[CH:22][C:23]=1[CH2:24][CH2:25][N:26]([CH2:29][CH3:30])[CH2:27][CH3:28]

Participants

3

Reactant 2

HCID 59691547(2-Chloro-4-trifluoromethyl-phenoxy)-acetic acidHCID 596916173-Chloro-4-(2-diethylaminoethyl)phenylamine

Product 1

HCID 10073080n-[3-Chloro-4-(2-diethylamino-ethyl)-phenyl]-2-(2-chloro-4-trifluoromethyl-phenoxy)-acetamide

Procedure

Prepared analogously to Example 143 starting from (2-chloro-4-trifluoromethyl-phenoxy)-acetic acid (Z2b) and 3-chloro-4-(2-diethylamino-ethyl)-phenylamine (Z44d). The reaction mixture was poured onto ice water and the aqueous phase was extracted with EtOAc. The org. phase was dried over sodium sulphate and evaporated down i. vac. The residue was purified by column chromatography (Alox, neutral, act. II-III, gradient petroleum ether/EtOAc 5:2→1:1).

Workup

  1. additionThe reaction mixture was poured onto ice water
  2. extractionthe aqueous phase was extracted with EtOAc
  3. dry with materialphase was dried over sodium sulphate
  4. customevaporated down i
  5. customThe residue was purified by column chromatography (Alox, neutral, act. II-III, gradient petroleum ether/EtOAc 5:2→1:1)

Sources & evidence

ORD record
ord-de032a7c47c9431a9127f7dd7c236cf7
Source dataset
uspto-grants-2008_04
Patent number
US07351719B2

Reaction notes

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