Ethyl isothiocyanate → HCID 86677611, compound

HRID 1484452Notes

Reaction equation

HRID 1484452 reaction equation
[CH2:1]([CH:3]1[CH2:7][NH:6][N:5]=[CH: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[CH2:4][CH:3]([CH2:1][CH3:2])[CH:7]=[N:6]1)=[S:12])[CH3:9]

Participants

4

Reactant 2

HCID 10966Ethyl isothiocyanateHCID 59339316HCID 59339316, compound

Product 1

HCID 86677611HCID 86677611, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2.68 g (1 mol equiv.) 4-Ethyl-4,5-dihydro-1H-pyrazole (synthesized as described in WO 2008/034863) and 3.11 mL (1.3 mol equiv.) ethyl isothiocyanate were added to 20 mL ethanol. The reaction mixture was refluxed overnight, silica gel was added and volatiles were removed under reduced pressure. Purification by flash chromatography on silica gel (Et2O:PA=1:3) afforded 1.80 g (36%) 4-ethyl-4,5-dihydro-pyrazole-1-carbothioic acid ethylamide. 1H NMR (400 MHz, CDCl3) δ 0.99 (t, J=7.5 Hz, 3H), 1.25 (t, J=7.2 Hz, 3H), 1.47-1.71 (m, 2H), 3.08-3.18 (m, 1H), 3.63-3.72 (m, 2H), 3.86 (dd, J=11.5, 7.1 Hz, 1H), 4.25 (t, J=11.5 Hz, 1H), 6.90 (d, J=1.5 Hz, 1H), 7.12 (br.s., 1H).

Workup

  1. temperatureThe reaction mixture was refluxed overnight
  2. additionsilica gel was added
  3. customvolatiles were removed under reduced pressure
  4. customPurification by flash chromatography on silica gel (Et2O:PA=1:3)

Sources & evidence

ORD record
ord-b29fa679e24542f3aff36c386f79bf13
Source dataset
uspto-grants-2016_08
Patent number
US09422244B2

Reaction notes

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