Hydrochloric Acid → HCID 54761408, compound

HRID 1746258Notes

Reaction equation

HRID 1746258 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]1[CH:22]=[C:23]([NH2:31])[CH:24]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:26]=1.C(N(CC)C(C)C)(C)C.Cl.C([O-])(O)=O.[Na+]>ClCCl>[F:20][C:21]1[CH:22]=[C:23]([NH:31][C:17]([C:10]2[CH:9]=[C:8]([C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=3)[O:12][C:11]=2[C:13]([F:16])([F:15])[F:14])=[O:18])[CH:24]=[C:25]([C:27]([F:29])([F:30])[F:28])[CH:26]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 27359133-Amino-5-fluorobenzotrifluorideHCID 27366415-(4-chlorophenyl)-2-(trifluoromethyl)furan-3-carbonyl chloride

Product 1

HCID 54761408HCID 54761408, compoundYield 26.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-(4-Chloro-phenyl)-2-trifluoromethyl-furan-3-carbonyl chloride (0.200 g) was added to a solution of 3-fluoro-5-trifluoromethyl-phenylamine (0.105 g) and N,N-diisopropylethylamine (0.102 mL) in dichloromethane (5 mL). After stirring at room temperature for 1 day, the reaction underwent an aqueous acidic (dilute HCl, 2×15 mL) and basic (dilute NaHCO3, 2×15 mL) workup followed by washing with brine (saturated NaCl, 2×15 mL), drying over MgSO4, and concentration. The crude compound was triturated with hexanes/ethyl ether (1:1) to afford the title compound (0.069 g, 24% yield). 1H NMR (CDCl3) δ 7.69 (d, 1H, J=0.02 Hz), 7.68 (s, 1H), 7.67 (d, 2H, J=0.017 Hz), 7.53 (s, 1H), 7.47 (d, 2H, J=0.017 Hz), 7.16 (d, 1H. J=0.02 Hz), 7.02 (s, 1H). ES-MS negative Q1 (m/z) 451.

Workup

  1. washby washing with brine (saturated NaCl, 2×15 mL)
  2. dry with materialdrying over MgSO4, and concentration
  3. customThe crude compound was triturated with hexanes/ethyl ether (1:1)

Sources & evidence

ORD record
ord-8b3447d2d366469891bb2eed2825d3d8
Source dataset
uspto-grants-2015_10
Patent number
US09149527B2

Reaction notes

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