Ethyl Acetate → HCID 63243696, compound

HRID 1615595Notes

Reaction equation

HRID 1615595 reaction equation
F[C:2]1[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][C:3]=1[C:4]#[N:5].[NH2:14][CH2:15][C:16]1[CH:20]=[CH:19][S:18][CH:17]=1.C(N(C(C)C)CC)(C)C.C(OCC)(=O)C>FC(C1C=CC=CC=1)(F)F>[S:18]1[CH:19]=[CH:20][C:16]([CH2:15][NH:14][C:2]2[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][C:3]=2[C:4]#[N:5])=[CH:17]1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 5210162-Fluoro-5-(trifluoromethyl)benzonitrileHCID 27763813-Thiophenemethylamine

Product 1

HCID 63243696HCID 63243696, compoundYield 85.9%

Reagents, catalysts & solvents 1

HCID 7368(Trifluoromethyl)benzeneSolvent

Conditions

Temperature
160 °C

Procedure

To a solution of 2-fluoro-5-trifluoromethylbenzonitrile 1A (1.11 g, 5.87 mmol) and 3-(aminomethyl)thiophene 1B (1.0 g, 8.85 mmol) in trifluoromethylbenzene (10 mL) was added diisopropylethylamine (2.3 g, 17.8 mmol). The reaction mixture was heated in a microwave reactor at 160° C. for 30 minutes. Ethyl acetate (100 mL) was added and the organic layer was washed with 1 N hydrochloric acid and brine. The organic layer was dried over sodium sulfate. The organic solvent was evaporated under reduced pressure to provide 2-[(thiophen-3-yl-methyl)amino]-5-trifluoromethylbenzonitrile 1C (1.42 g, 5.04 mmol) which was used in the next step without further purification.

Workup

  1. washthe organic layer was washed with 1 N hydrochloric acid and brine
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. customThe organic solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-e88c428157004e3b905b6867004cf8c5
Source dataset
uspto-grants-2014_07
Patent number
US08765757B2

Reaction notes

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