Hydrochloric Acid → 2-Methyl-5-phenyl-furan-3-carboxylic acid (3,5-bis-trifluoromethyl-phenyl)-amide

HRID 1023747Notes

Reaction equation

HRID 1023747 reaction equation
[CH3:1][C:2]1[O:3][C:4]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:5][C:6]=1[C:7](Cl)=[O:8].[F:16][C:17]([F:30])([F:29])[C:18]1[CH:19]=[C:20]([NH2:28])[CH:21]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:23]=1.C(N(CC)C(C)C)(C)C.Cl.C([O-])(O)=O.[Na+]>ClCCl>[F:16][C:17]([F:29])([F:30])[C:18]1[CH:19]=[C:20]([NH:28][C:7]([C:6]2[CH:5]=[C:4]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[O:3][C:2]=2[CH3:1])=[O:8])[CH:21]=[C:22]([C:24]([F:25])([F:27])[F:26])[CH:23]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 9480Benzenamine, 3,5-bis(trifluoromethyl)-HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 27764322-Methyl-5-phenylfuran-3-carbonyl chloride

Product 1

HCID 547614072-Methyl-5-phenyl-furan-3-carboxylic acid (3,5-bis-trifluoromethyl-phenyl)-amideYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Methyl-5-phenyl-furan-3-carbonyl chloride (0.025 g) was added to a solution of 3,5-bis-trifluoromethyl-phenylamine (0.024 g) and N,N-diisopropylethyl-amine (0.018 mL) in dichloromethane (5 mL). After stirring at room temperature for 1 day, the reaction underwent an aqueous acidic (dilute HCl, 2×5 mL) and basic (dilute NaHCO3, 2×5 mL) workup followed by washing with brine (saturated NaCl, 2×5 mL), drying over MgSO4, and concentration. The crude compound was purified by passing through a silica gel plug eluting with hexanes/ethyl acetate (2:1) to afford the title compound (0.035 g, 82% yield). ES-MS negative Q1 (m/z) 412.

Workup

  1. washby washing with brine (saturated NaCl, 2×5 mL)
  2. dry with materialdrying over MgSO4, and concentration
  3. customThe crude compound was purified
  4. washeluting with hexanes/ethyl acetate (2:1)

Sources & evidence

ORD record
ord-94dad2f49c82444d9d999326b6328b89
Source dataset
uspto-grants-2014_05
Patent number
US08722731B2

Reaction notes

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