Triethylamine → 4-Chloro-1,3-dimethylpyrazole-5-carboxamide

To a stirred mixture of 4-[4-(1,1,2,2-tetrafluoroethoxy)phenoxy]benzylamine (359 mg, 1.14 mM), triethylamine (136 mg, 1.35 mM) and toluene (20 ml) was added dropwise a solution (10 ml) of 4-chloro-1,3-dimethylpyrazole-5-carbonyl chloride (200 mg, 1.04 mM) in toluene at 0°-10° C., and the mixture was stirred for 3 h at room temperature. The mixture was poured into ice water, and the mixture was extracted with toluene. The extract was washed with saturated sodium hydrogen carbonate solution, saturated ammonium chloride solution and brine, dried with magnesium sulfate, and concentrated in vacuo. The residue was chromatographed over silica gel to give N-{4-[1,1,2,2,-tetrafluoroethoxy)phenoxy]benzyl}-4-chloro-1,3-dimethylpyrazole-5-carboxamide (420 mg, 86%) as colorless crystals, m.p. 101.3° C.

1. extractionthe mixture was extracted with toluene
2. washThe extract was washed with saturated sodium hydrogen carbonate solution, saturated ammonium chloride solution and brine
3. dry with materialdried with magnesium sulfate
4. concentrationconcentrated in vacuo
5. customThe residue was chromatographed over silica gel

ORD record

ord-427dab70776e4c49a92c6f9c1532e95a

Source dataset

uspto-grants-1993_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05264448