Triethylamine → N-Methoxy-N-methyl-2-(4'-trifluoromethyl-biphenyl-4-yl)-acetamide

HRID 1669287Notes

Reaction equation

HRID 1669287 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([CH2:15][C:16]([OH:18])=O)=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.N1(C([N:28]2[CH:32]=CC=N2)=O)C=CN=C1.C(N(CC)CC)C.[C:40](OCC)(=[O:42])C.CCCCCC>O1CCCC1.CN(C)C=O.C(OCC)(=O)C>[CH3:40][O:42][N:28]([CH3:32])[C:16](=[O:18])[CH2:15][C:12]1[CH:13]=[CH:14][C:9]([C:6]2[CH:7]=[CH:8][C:3]([C:2]([F:19])([F:1])[F:20])=[CH:4][CH:5]=2)=[CH:10][CH:11]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 13686857(1H-Imidazol-1-yl)(1H-pyrazol-1-yl)methanoneHCID 21226206Ethyl acetate hexaneHCID 222801814-[4-(Trifluoromethyl)phenyl]phenylacetic acid2×

Product 1

HCID 86085431N-Methoxy-N-methyl-2-(4'-trifluoromethyl-biphenyl-4-yl)-acetamideYield 78%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (4′-trifluoromethyl-biphenyl-4-yl)-acetic acid (0.276 g, 0.99 mmol) in tetrahydro-furan (1 mL) is added imidazol-1-yl-pyrazol-1-yl-methanone (0.176 g, 1.1 mmol) and stirred for thirty minutes. A solution of O, N-dimethyl-hydroxylamine hydrochloride (0.107 g, 1.1 mmol) and triethyl-amine (0.15 mL, 1.1 mmol) in N,N-dimethyl-formamide (4 mL) is added to (4′-trifluoromethyl-biphenyl-4-yl)-acetic acid solution and stir sixteen hours, diluted with ethyl acetate, washed with water two times then brine. Organics are dried over sodium sulfate, filtered and concentrated. Column chromatography on silica gel with 0-60% ethyl acetate/hexane gradient gives 0.250 g (0.77 mmol, 78%) of title compound.

Workup

  1. stirringstir sixteen hours
  2. washwashed with water two times
  3. dry with materialOrganics are dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-8377b07098c245f1ac36151df0d486ea
Source dataset
uspto-grants-2011_08
Patent number
US07989457B2

Reaction notes

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