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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 528959Generated: October 27, 2026

Ethyl Acetate → 4-chloro-N,N-dipropyl-5-(trifluoromethyl)-1H-pyrazol-3-amine

https://huagongshe.com/reaction/528959

Reaction equation

Participants

RoleNameHCIDCharge
ReactantEthyl AcetateHCID 8857—
ReactantAmmonium ChlorideHCID 25517—
ReactantChlorosuccinimideHCID 31398—
ReactantN,N-dipropyl-5-(trifluoromethyl)-1H-pyrazol-3-amineHCID 71062423—
SolventDimethylformamideHCID 6228—
Product4-chloro-N,N-dipropyl-5-(trifluoromethyl)-1H-pyrazol-3-amineHCID 71062226100.4%

Reaction Conditions

Temperature100 °C

Reaction Steps

To N,N-dipropyl-5-(trifluoromethyl)-1H-pyrazol-3-amine (250 mg, 1.06 mmol) in DMF (5.3 mL) was added NCS (142 mg, 1.06 mmol). The resulting reaction mixture was stirred at 100° C. for 1 h and then poured into sat. aq. NH4Cl solution and EtOAc (1:1). The organic layer was washed sat. aq. NH4Cl solution (3×), and the combined aqueous layer was extracted with EtOAc (3×). The combined organic extracts were dried over Na2SO4, filtered and concentrated in vacuo to give the title compound (287 mg, 100%). 1H NMR (CDCl3) δ 3.23-3.14 (m, 4H), 1.59-1.44 (m, 4H), 0.88 (t, J=7.4 Hz, 6H); MS(ESI+) m/z 270.1 (M+H)+.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09346795B2
Source datasetuspto-grants-2016_05
ORD IDord-bca843eab8224bf283ca8175f85c0746
Source noteuspto-grants-2016_05