(e)-n-[4-(3-Bromo-propyl)-3-chloro-phenyl]-3-(2-chloro-4-trifluoromethyl-phenyl)-acrylamide → (e)-n-[3-Chloro-4-(3-diethylamino-propyl)-phenyl]-3-(2-chloro-4-trifluoromethyl-phenyl)-acrylamide

HRID 898631Notes

Reaction equation

HRID 898631 reaction equation
Br[CH2:2][CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:26])/[CH:13]=[CH:14]/[C:15]2[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][C:16]=2[Cl:25])=[CH:7][C:6]=1[Cl:27]>C(NCC)C.CCOC(C)=O>[Cl:27][C:6]1[CH:7]=[C:8]([NH:11][C:12](=[O:26])/[CH:13]=[CH:14]/[C:15]2[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][C:16]=2[Cl:25])[CH:9]=[CH:10][C:5]=1[CH2:4][CH2:3][CH2:2][N:11]([CH2:12][CH3:13])[CH2:8][CH3:7]

Participants

4

Reactant 1

HCID 87610233(e)-n-[4-(3-Bromo-propyl)-3-chloro-phenyl]-3-(2-chloro-4-trifluoromethyl-phenyl)-acrylamide

Product 1

HCID 59691692(e)-n-[3-Chloro-4-(3-diethylamino-propyl)-phenyl]-3-(2-chloro-4-trifluoromethyl-phenyl)-acrylamide

Reagents, catalysts & solvents 2

HCID 8021DiethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 0.290 g (0.603 mmol) (E)-N-[4-(3-bromo-propyl)-3-chloro-phenyl]-3-(2-chloro-4-trifluoromethyl-phenyl)-acrylamide (Z45d) in 2 mL diethylamine was heated to 100° C. in a sealed reaction vessel in the microwave for 5 min. The reaction mixture was diluted with EtOAc, the org. phase was washed with water, dried over sodium sulphate and evaporated down i. vac. The residue was triturated with ether, the precipitate was filtered off, washed with ether and dried in a HV.

Workup

  1. washphase was washed with water
  2. dry with materialdried over sodium sulphate
  3. customevaporated down i
  4. customThe residue was triturated with ether
  5. filtrationthe precipitate was filtered off
  6. washwashed with ether
  7. customdried in a HV

Sources & evidence

ORD record
ord-a804382e0dbb42df9fcaf6cef49aebde
Source dataset
uspto-grants-2008_04
Patent number
US07351719B2

Reaction notes

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