N,N-Dimethylaniline → HCID 15421643, compound

HRID 1360389Notes

Reaction equation

HRID 1360389 reaction equation
Br[CH2:2][CH2:3][C:4](Cl)=[O:5].CN(C)C1C=CC=CC=1.[F:16][C:17]([F:26])([F:25])[C:18]1[CH:24]=[CH:23][C:21]([NH2:22])=[CH:20][CH:19]=1.[OH-].[K+]>C(Cl)Cl.C(Cl)Cl.C(#N)C.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[F:16][C:17]([F:25])([F:26])[C:18]1[CH:19]=[CH:20][C:21]([N:22]2[CH2:2][CH2:3][C:4]2=[O:5])=[CH:23][CH:24]=1

Participants

8

Reactant 4

HCID 949N,N-DimethylanilineHCID 99644-(Trifluoromethyl)anilineHCID 14797Potassium HydroxideHCID 84944Propanoyl chloride, 3-bromo-

Product 1

HCID 15421643HCID 15421643, compoundYield 71%

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 6344DichloromethaneSolventHCID 21877088Acetonitrile methylene chlorideSolvent

Procedure

3-Bromopropanoyl chloride (3.13 mL, 31.0 mmol) and N,N-dimethylaniline (3.91 mL, 31.0 mmol) were dissolved in methylene chloride (30 ml), 4-trifluoromethylaniline (5 g, 31.0 mmol) was added dropwise at 0° C., and the mixture was stirred at room temperature for 2 hrs. Work-up of the reaction mixture according to a conventional method gave a crude product. The obtained crude product was dissolved in a mixed solvent (100 mL) of methylene chloride/acetonitrile (20/1), potassium hydroxide (2.28 g, 40.6 mmol) and tetrabutylammonium bromide (3.26 g, 6.76 mmol) were added, and the mixture was stirred overnight at room temperature. The solvent was evaporated and, after work-up according to a conventional method, the mixture was purified by silica gel column chromatography to give the title compound (4.6 g, 21.4 mmol, 71%).

Workup

  1. customgave a crude product
  2. customThe obtained crude product
  3. additionwere added
  4. stirringthe mixture was stirred overnight at room temperature
  5. customThe solvent was evaporated
  6. customthe mixture was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-261d692158a84608a3c95ce1e87c256c
Source dataset
uspto-grants-2011_02
Patent number
US07879863B2

Reaction notes

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