2-Chloro-4-trifluoromethylaniline → N-[3-chloro-4-(2-diethylamino-ethoxy)-phenyl]-2-(2-chloro-4-trifluoromethyl-phenylamino)-acetamide

HRID 898564Notes

Reaction equation

HRID 898564 reaction equation
Br.Br[CH2:3][C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15][N:16]([CH2:19][CH3:20])[CH2:17][CH3:18])=[C:9]([Cl:21])[CH:8]=1)=[O:5].[Cl:22][C:23]1[CH:28]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:26]=[CH:25][C:24]=1[NH2:33]>CN(C=O)C.O>[Cl:21][C:9]1[CH:8]=[C:7]([NH:6][C:4](=[O:5])[CH2:3][NH:33][C:24]2[CH:25]=[CH:26][C:27]([C:29]([F:30])([F:31])[F:32])=[CH:28][C:23]=2[Cl:22])[CH:12]=[CH:11][C:10]=1[O:13][CH2:14][CH2:15][N:16]([CH2:19][CH3:20])[CH2:17][CH3:18]

Participants

5

Reactant 2

HCID 1620012-Chloro-4-trifluoromethylanilineHCID 688779532-Bromo-n-[3-chloro-4-(2-diethylamino-ethoxy)-phenyl]-acetamide-hydrobromide

Product 1

HCID 10344989N-[3-chloro-4-(2-diethylamino-ethoxy)-phenyl]-2-(2-chloro-4-trifluoromethyl-phenylamino)-acetamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 0.228 g (0.511 mmol) of 2-bromo-N-[3-chloro-4-(2-diethylamino-ethoxy)-phenyl]-acetamide-hydrobromide (intermediate product Z1c) and 0.200 g (1.023 mmol) of 2-chloro-4-trifluoromethyl-phenylamine in 5 mL DMF was stirred for 16 hours at 90° C. and then for 24 hours at 120° C. The reaction mixture was cooled to RT, diluted with water and exhaustively extracted with EtOAc. The combined org. extracts were dried over magnesium sulphate and evaporated down i. vac. The residue was dissolved in DMF and purified by HPLC-MS (Stable Bond C18; 3.5 μm; water:acetonitrile:formic acid 9:1:0.01→1:9:0.01 over 9 min).

Workup

  1. extractionexhaustively extracted with EtOAc
  2. dry with materialextracts were dried over magnesium sulphate
  3. customevaporated down i
  4. dissolutionThe residue was dissolved in DMF
  5. custompurified by HPLC-MS (Stable Bond C18; 3.5 μm; water:acetonitrile:formic acid 9:1:0.01→1:9:0.01 over 9 min)

Sources & evidence

ORD record
ord-2d728526d922429c9e92297b3efee6e1
Source dataset
uspto-grants-2008_04
Patent number
US07351719B2

Reaction notes

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