Ethyl isothiocyanate → HCID 86677608, compound

HRID 1484438Notes

Reaction equation

HRID 1484438 reaction equation
[CH2:1]([C:3]1[CH2:7][CH2:6][NH:5][N:4]=1)[CH3:2].[CH2:8]([N:10]=[C:11]=[S:12])[CH3:9]>C(O)C>[CH2:8]([NH:10][C:11]([N:5]1[CH2:6][CH2:7][C:3]([CH2:1][CH3:2])=[N:4]1)=[S:12])[CH3:9]

Participants

4

Reactant 2

HCID 10966Ethyl isothiocyanateHCID 5581491H-Pyrazole, 3-ethyl-4,5-dihydro-

Product 1

HCID 86677608HCID 86677608, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.25 g (1 mol equiv.) 3-Ethyl-4,5-dihydro-1H-pyrazole (synthesized as described in WO 2008/034863) and 1.45 ml (1.3 mol equiv.) ethyl isothiocyanate were added to 10 mL ethanol. The reaction mixture was refluxed for 5 hours, silica gel was added and volatiles were removed in vacuo. Purification by flash chromatography on silica gel (Et2O:PA=1:1) afforded 1.54 g (65%) 3-ethyl-4,5-dihydro-pyrazole-1-carbothioic acid ethylamide. 1H NMR (400 MHz, CDCl3) δ 1.18 (t, J=7.5 Hz, 3H), 1.25 (t, J=7.2 Hz, 3H), 2.38 (q, J=7.5 Hz, 2H), 2.83 (t, J=9.9 Hz, 2H), 3.63-3.72 (m, 2H), 4.19 (t, J=9.9 Hz, 2H), 7.06 (br.s., 1H).

Workup

  1. temperatureThe reaction mixture was refluxed for 5 hours
  2. additionsilica gel was added
  3. customvolatiles were removed in vacuo
  4. customPurification by flash chromatography on silica gel (Et2O:PA=1:1)

Sources & evidence

ORD record
ord-4623c21889f245c490c8bc00bb6bc209
Source dataset
uspto-grants-2016_08
Patent number
US09422244B2

Reaction notes

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