Ethyl isothiocyanate → HCID 86677609, compound

HRID 1484445Notes

Reaction equation

HRID 1484445 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([CH:6]2[NH:10][N:9]=[CH:8][CH2:7]2)=[CH:2]1.[CH2:11]([N:13]=[C:14]=[S:15])[CH3:12]>C(O)C>[CH2:11]([NH:13][C:14]([N:10]1[CH:6]([C:3]2[CH:4]=[CH:5][S:1][CH:2]=2)[CH2:7][CH:8]=[N:9]1)=[S:15])[CH3:12]

Participants

4

Reactant 2

HCID 10966Ethyl isothiocyanateHCID 59339300HCID 59339300, compound

Product 1

HCID 86677609HCID 86677609, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.82 g (1 mol equiv.) 5-Thiophen-3-yl-4,5-dihydro-1H-pyrazole (synthesized as described in WO 2008/034863) and 1.36 mL (1.3 mol equiv.) ethyl isothiocyanate were added to 15 mL ethanol. The reaction mixture was refluxed for 5 hours, and subsequently concentrated on silica gel under reduced pressure. Purification by flash chromatography on silica gel (Et2O:PA=1:1) afforded 0.70 g (26%) 5-thiophen-3-yl-4,5-dihydro-pyrazole-1-carbothioic acid ethylamide. 1H NMR (400 MHz, CDCl3) δ 1.24 (t, J=7.2 Hz, 3H), 2.86 (ddd, J=18.5, 3.3, 1.7 Hz, 1H), 3.39 (ddd, J=18.5, 11.4, 1.7 Hz, 1H), 3.56-3.77 (m, 2H), 6.01 (dd, J=11.4, 3.3 Hz, 1H), 6.93 (dd, J=5.0, 1.0 Hz, 1H), 7.02 (t, J=1.7 Hz, 1H), 7.13 (m, 1H), 7.26 (m, 1H).

Workup

  1. temperatureThe reaction mixture was refluxed for 5 hours
  2. concentrationsubsequently concentrated on silica gel under reduced pressure
  3. customPurification by flash chromatography on silica gel (Et2O:PA=1:1)

Sources & evidence

ORD record
ord-12fb90681c7840039bf170aaba863571
Source dataset
uspto-grants-2016_08
Patent number
US09422244B2

Reaction notes

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