Triethylamine → 2-Methyl-4'-trifluoromethyl-biphenyl-4-carboxylic acid methoxy-methyl-amide

HRID 1669338Notes

Reaction equation

HRID 1669338 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([C:8](O)=[O:9])[CH:5]=[CH:4][C:3]=1[C:11]1[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=1.N1(C(N2C=CN=C2)=O)C=CN=C1.Cl.[CH3:34][O:35][NH:36][CH3:37].C(N(CC)CC)C.CONC>O1CCCC1.CN(C)C=O.C(OCC)(=O)C>[CH3:34][O:35][N:36]([CH3:37])[C:8]([C:6]1[CH:5]=[CH:4][C:3]([C:11]2[CH:12]=[CH:13][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:15][CH:16]=2)=[C:2]([CH3:1])[CH:7]=1)=[O:9]

Participants

9

Reactant 5

HCID 8471TriethylamineHCID 14232N,O-DimethylhydroxylamineHCID 682631,1'-CarbonyldiimidazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 231205192-Methyl-4'-(trifluoromethyl)[1,1'-biphenyl]-4-carboxylic acid2×

Product 1

HCID 866203622-Methyl-4'-trifluoromethyl-biphenyl-4-carboxylic acid methoxy-methyl-amideYield 23%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Combine 2-methyl-4′-trifluoromethyl-biphenyl-4-carboxylic acid (2.31 g, 8.25 mmol) and di-imidazol-1-yl-methanone (1.47 g, 9.08 mmol) in tetrahydro-furan (15 mL) and stir twenty minutes. In a separate reaction vessel, combine O,N-dimethyl-hydroxylamine hydrochloride (0.885 g, 9.08 mmol) and triethyl-amine (1.3 mL, 9.08 mmol) in N,N-dimethyl-formamide (20 mL). Add O,N-dimethyl-hydroxylamine solution to the 2-methyl-4′-trifluoromethyl-biphenyl-4-carboxylic acid solution and stir sixteen hours. Dilute reaction with ethyl acetate, wash with 0.5 N HCl, 0.1N NaOH, and saturated sodium chloride solution. Dry organic fraction with Na2SO4, filter and concentrate under reduced pressure to provide 0.6 g (23%) of title compound.

Workup

  1. customIn a separate reaction vessel
  2. additionDilute
  3. washwash with 0.5 N HCl, 0.1N NaOH, and saturated sodium chloride solution
  4. filtrationDry organic fraction with Na2SO4, filter
  5. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-c529bf608bb349efb577c140cde43937
Source dataset
uspto-grants-2011_08
Patent number
US07989457B2

Reaction notes

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