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

HRID 528959Notes

Reaction equation

HRID 528959 reaction equation
[CH2:1]([N:4]([CH2:14][CH2:15][CH3:16])[C:5]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[NH:7][N:6]=1)[CH2:2][CH3:3].C1C(=O)N([Cl:24])C(=O)C1.[NH4+].[Cl-].CCOC(C)=O>CN(C=O)C>[Cl:24][C:9]1[C:5]([N:4]([CH2:1][CH2:2][CH3:3])[CH2:14][CH2:15][CH3:16])=[N:6][NH:7][C:8]=1[C:10]([F:12])([F:13])[F:11]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 31398ChlorosuccinimideHCID 71062423N,N-dipropyl-5-(trifluoromethyl)-1H-pyrazol-3-amine

Product 1

HCID 710622264-chloro-N,N-dipropyl-5-(trifluoromethyl)-1H-pyrazol-3-amineYield 100.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

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)+.

Workup

  1. customThe resulting reaction mixture
  2. washThe organic layer was washed sat. aq. NH4Cl solution (3×)
  3. extractionthe combined aqueous layer was extracted with EtOAc (3×)
  4. dry with materialThe combined organic extracts were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bca843eab8224bf283ca8175f85c0746
Source dataset
uspto-grants-2016_05
Patent number
US09346795B2

Reaction notes

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