Trifluoroacetic acid → 5-(4-Chlorophenyl)-thiophene-2-carboxylic acid (2-oxoethyl)amide

HRID 2384875Notes

Reaction equation

HRID 2384875 reaction equation
FC(F)(F)C(O)=O.C([O:10][CH:11](OCC)[CH2:12][NH:13][C:14]([C:16]1[S:17][C:18]([C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=2)=[CH:19][CH:20]=1)=[O:15])C>O>[O:10]=[CH:11][CH2:12][NH:13][C:14]([C:16]1[S:17][C:18]([C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=2)=[CH:19][CH:20]=1)=[O:15]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 1317294095-(4-Chlorophenyl)-N-(2,2-diethoxyethyl)thiophene-2-carboxamide

Product 1

HCID 866292045-(4-Chlorophenyl)-thiophene-2-carboxylic acid (2-oxoethyl)amideYield 95.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Add water (21 mL) followed by trifluoroacetic acid (100 g) to a 250 mL three-necked round bottom flask equipped with an overhead stirrer, nitrogen inlet/outlet, and thermocouple. To the stirring TFA solution, add 5-(4-chlorophenyl)-thiophene-2-carboxylic acid (2,2-diethyoxyethyl) amide (25 g, 0.07 mol) in one portion. Stir the reaction mixture for 4 h, pour onto ice/water (1200 mL), and stir for 1.25 h. Filter the resulting slurry and rinse the solid with water (500 mL) and heptane (500 mL), and then dry to give 18.65 g (95%) of the title compound as a yellow-white solid. LC-MS/ES m/z (35Cl)=278 (M−H)−. 1H NMR (500 MHz, CDCl3): δ 4.40 (d, J=4.0 Hz, 2H), 6.69 (bs, 1H), 7.26 (d, J=3.0 Hz, 1H), 7.40 (d, J=9.0 Hz, 2H), 7.53-7.58 (m, 3H), 9.78 (s, 1H).

Workup

  1. customequipped with an overhead stirrer, nitrogen inlet/outlet
  2. additionpour onto ice/water (1200 mL)
  3. stirringstir for 1.25 h
  4. filtrationFilter the resulting slurry
  5. washrinse the solid with water (500 mL) and heptane (500 mL)
  6. customdry

Sources & evidence

ORD record
ord-2fc154d0d6154e8a9541c0f66165400f
Source dataset
uspto-grants-2012_09
Patent number
US08263772B2

Reaction notes

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