Tetrahydrofuran → HCID 178449877, compound

HRID 570746

Reaction equation

HRID 570746 reaction equation
[F:1][C:2]([F:13])([F:12])[CH2:3][O:4][C:5]1[CH:11]=[CH:10][C:8]([NH2:9])=[CH:7][CH:6]=1.C([N:16]([CH2:19][CH3:20])CC)C.[CH2:21]1COC[CH2:22]1.C(OCC)(=O)C>O>[F:1][C:2]([F:12])([F:13])[CH2:3][O:4][C:5]1[CH:11]=[CH:10][C:8]([NH:9][C:19](=[NH:16])[CH2:20][CH2:21][CH3:22])=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 27771194-(2,2,2-Trifluoroethoxy)aniline

Product 1

HCID 178449877HCID 178449877, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of ethyl butylimidate hydrochloride (10.0 g), 4-(2,2,2-trifluoroethoxy)aniline (12.6 g), triethylamine (6.67 g) and THF (250 mL) was stirred at 70° C. for 2 days. To the reaction mixture were added ethyl acetate and water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to aminopropylsilane-bonded silica gel column chromatography (ethyl acetate/hexane) to give the title compound (4.80 g) as a solid.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0af3bb64acb847fab8f831589a93f56d
Source dataset
uspto-grants-2015_05
Patent number
US09023858B2

Linked notes

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