Hydrochloric Acid → HCID 86683824, compound

HRID 1746256Notes

Reaction equation

HRID 1746256 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][C:11]([C:13]([F:16])([F:15])[F:14])=[C:10]([C:17](Cl)=[O:18])[CH:9]=2)=[CH:4][CH:3]=1.[F:20][C:21]([F:34])([F:33])[C:22]1[CH:23]=[C:24]([NH2:32])[CH:25]=[C:26]([C:28]([F:31])([F:30])[F:29])[CH:27]=1.C(N(CC)C(C)C)(C)C.Cl.C([O-])(O)=O.[Na+]>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][C:11]([C:13]([F:16])([F:15])[F:14])=[C:10]([C:17]([NH:32][C:24]3[CH:25]=[C:26]([C:28]([F:29])([F:30])[F:31])[CH:27]=[C:22]([C:21]([F:20])([F:33])[F:34])[CH:23]=3)=[O:18])[CH:9]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 9480Benzenamine, 3,5-bis(trifluoromethyl)-HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 27366415-(4-chlorophenyl)-2-(trifluoromethyl)furan-3-carbonyl chloride

Product 1

HCID 86683824HCID 86683824, compoundYield 63.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-(4-Chloro-phenyl)-2-trifluoromethyl-furan-3-carbonyl chloride (0.050 g) was added to a solution of 3,5-bis-trifluoromethyl-phenylamine (0.034 g) and N,N-diisopropylethylamine (0.026 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 column chromatography eluting with ethyl acetate/hexanes (4:1) to afford the title compound (0.047 g, 58% yield). 1H NMR (CDCl3) δ 8.12 (s, 2H), 7.83 (bs, 1H), 7.70 (s, 1H), 7.68 (d, 2H, J=0.017 Hz), 7.47 (d, 2H, J=0.017 Hz), 7.03 (s, 1H). ES-MS negative Q1 (m/z) 501.

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 by column chromatography
  4. washeluting with ethyl acetate/hexanes (4:1)

Sources & evidence

ORD record
ord-77008bad67a34e698389e9db634a6fbd
Source dataset
uspto-grants-2015_10
Patent number
US09149527B2

Reaction notes

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