Hydrochloric Acid → HCID 54761405, compound

HRID 1746255Notes

Reaction equation

HRID 1746255 reaction equation
[C:1]1([C:7]2[O:11][C:10]([C:12]([F:15])([F:14])[F:13])=[C:9]([C:16](Cl)=[O:17])[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:19][C:20]([F:33])([F:32])[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:19][C:20]([F:32])([F:33])[C:21]1[CH:22]=[C:23]([NH:31][C:16]([C:9]2[CH:8]=[C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[O:11][C:10]=2[C:12]([F:15])([F:14])[F:13])=[O:17])[CH:24]=[C:25]([C:27]([F:28])([F:30])[F:29])[CH:26]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 9480Benzenamine, 3,5-bis(trifluoromethyl)-HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 534353995-Phenyl-2-(trifluoromethyl)-3-furancarbonyl chloride

Product 1

HCID 54761405HCID 54761405, compoundYield 92.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

An excess of 5-phenyl-2-trifluoromethyl-furan-3-carbonyl chloride (1 g, 3.6 mmol) was added to a solution of 3,5-bis-trifluoromethyl-phenylamine (0.758 g, 3.3 mmol) and N,N-diisopropylethylamine (0.58 mL) in dichloromethane (50 mL). After stirring at room temperature for 1 day, the reaction underwent an aqueous acidic (dilute HCl, 2×30 mL) and basic (dilute NaHCO3, 2×30 mL) workup followed by washing with brine (saturated NaCl, 2×30 mL), drying over MgSO4, and concentration. The crude compound was purified by passing through a silica gel plug eluting with ethyl acetate/hexanes (2:1) to afford the title compound (1.42 g, 92% yield). ES-MS negative Q1 (m/z) 466.

Workup

  1. washby washing with brine (saturated NaCl, 2×30 mL)
  2. dry with materialdrying over MgSO4, and concentration
  3. customThe crude compound was purified
  4. washeluting with ethyl acetate/hexanes (2:1)

Sources & evidence

ORD record
ord-91915a3060b64bbbbc89327831d10eb4
Source dataset
uspto-grants-2015_10
Patent number
US09149527B2

Reaction notes

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