Water → 2-(4-Chlorophenyl)-6H,7H-thieno[2,3-c]pyridin-7-one

HRID 2384877Notes

Reaction equation

HRID 2384877 reaction equation
FC(F)(F)S(O)(=O)=O.O=[CH:10][CH2:11][NH:12][C:13]([C:15]1[S:16][C:17]([C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=2)=[CH:18][CH:19]=1)=[O:14].O>>[Cl:26][C:23]1[CH:24]=[CH:25][C:20]([C:17]2[S:16][C:15]3[C:13](=[O:14])[NH:12][CH:11]=[CH:10][C:19]=3[CH:18]=2)=[CH:21][CH:22]=1

Participants

4

Reactant 3

HCID 962WaterHCID 62406Trifluoromethanesulfonic acidHCID 866292045-(4-Chlorophenyl)-thiophene-2-carboxylic acid (2-oxoethyl)amide

Product 1

HCID 576495192-(4-Chlorophenyl)-6H,7H-thieno[2,3-c]pyridin-7-oneYield 100%

Conditions

Temperature
95 °C

Procedure

Add trifluoromethane sulfonic acid (3 mL, 0.03 mol) and 5-(4-chlorophenyl)-thiophene-2-carboxylic acid (2-oxoethyl) amide (1 g, 0.004 mol) to a 25 mL three-necked round bottom flask equipped with a stir bar, Dean-Stark trap, nitrogen inlet/outlet, and thermocouple. Heat the reaction mixture to 95° C. for 2 h, then cool to 40° C., and pour onto cold water (20 mL, 1.11 mol). Stir the mixture for 10 min. Filter the resulting slurry and rinse the solids with water (100 mL). Dry to afford crude 2-(4-chlorophenyl)-6H-thieno[2,3-c]pyridine-7-one (0.95 g, 0.004 mol) as a brown solid. LC-MS/ES m/z (35Cl) 262 [M+1]+.

Workup

  1. customequipped with a stir bar
  2. temperaturecool to 40° C.
  3. filtrationFilter the resulting slurry
  4. washrinse the solids with water (100 mL)
  5. customDry

Sources & evidence

ORD record
ord-b16b44aeeb7f4af8b1841efd9275d9ea
Source dataset
uspto-grants-2012_09
Patent number
US08263772B2

Reaction notes

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