1,2-Dichloroethane → N-[3,5-Bis(trifluoromethyl)phenyl]-2-chloroacetamide

HRID 1094709Notes

Reaction equation

HRID 1094709 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:4]=[C:5]([CH:7]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:9]=1)[NH2:6].[Cl:16][CH2:17][C:18](O)=[O:19].C(Cl)CCl>C(Cl)Cl.CN(C1C=CN=CC=1)C>[F:1][C:2]([F:14])([F:15])[C:3]1[CH:4]=[C:5]([NH:6][C:18](=[O:19])[CH2:17][Cl:16])[CH:7]=[C:8]([C:10]([F:11])([F:12])[F:13])[CH:9]=1

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 300Chloroacetic AcidHCID 9480Benzenamine, 3,5-bis(trifluoromethyl)-

Product 1

HCID 1800613N-[3,5-Bis(trifluoromethyl)phenyl]-2-chloroacetamideYield 74%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3,5-bis(trifluoromethyl)aniline (3.74 g, 16.3 mmol) in DCM (60 mL) was added chloroacetic acid (2.31 g, 24.4 mmol), EDC (5.0 g, 32.6 mmol) and DMAP (cat.). The reaction mixture was stirred at RT overnight. The contents were transferred to a separatory funnel and DCM layer was washed with saturated NaHCO3 solution, dried over anhydrous Na2SO4. The crude product was purified by flash column chromatography using 3:1 Pet. Ether:DCM in. Purified product was isolated as a white solid weighing 3.67 g (yield: 74%).

Workup

  1. customThe contents were transferred to a separatory funnel
  2. washDCM layer was washed with saturated NaHCO3 solution
  3. dry with materialdried over anhydrous Na2SO4
  4. customThe crude product was purified by flash column chromatography
  5. customPurified product was isolated as a white solid

Sources & evidence

ORD record
ord-459c78ec107341c893b833c1aa35fece
Source dataset
uspto-grants-2012_03
Patent number
US08133998B2

Reaction notes

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