Trifluoroacetic acid → 3-amino-5-(4-chlorophenyl)thiophene-2-carboxamide

HRID 1375055Notes

Reaction equation

HRID 1375055 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:12]=[C:11]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)[S:10][C:9]=1[C:20](=[O:22])[NH2:21])(C)(C)C.C(O)(C(F)(F)F)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[NH2:7][C:8]1[CH:12]=[C:11]([C:13]2[CH:14]=[CH:15][C:16]([Cl:19])=[CH:17][CH:18]=2)[S:10][C:9]=1[C:20]([NH2:21])=[O:22]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 86760365HCID 86760365, compound

Product 1

HCID 27563903-amino-5-(4-chlorophenyl)thiophene-2-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1c (250 mg, 0.71 mmol) in CH2Cl2 (10 mL) was added TFA (1 mL). The resultant solution was stirred for 1 h, then mixed with saturated NaHCO3 solution (60 mL), and extracted with ethyl acetate (50 mL, 3×). The combined organic phases were dried over MgSO4, filtered, and concentrated. Flash chromatography (hexanes/ethyl acetate, 1:1) then provided compound 1d as a yellow solid: MS (ES) 253 (M+H)+.

Workup

  1. extractionextracted with ethyl acetate (50 mL, 3×)
  2. dry with materialThe combined organic phases were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-adc53e5856ad463f81c5e6c93d6df7d6
Source dataset
uspto-grants-2007_01
Patent number
US07166639B2

Reaction notes

Loading…