Methyl iodide → HCID 67359394, compound

HRID 1484453Notes

Reaction equation

HRID 1484453 reaction equation
[CH2:1]([NH:3][C:4]([N:6]1[CH2:10][CH:9]([CH2:11][CH3:12])[CH:8]=[N:7]1)=[S:5])[CH3:2].I[CH3:14]>CO>[CH3:14][S:5][C:4]([N:6]1[CH2:10][CH:9]([CH2:11][CH3:12])[CH:8]=[N:7]1)=[N:3][CH2:1][CH3:2]

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 86677611HCID 86677611, compound

Product 1

HCID 67359394HCID 67359394, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

1.80 g (1 mol equiv.) 4-Ethyl-4,5-dihydro-pyrazole-1-carbothioic acid ethylamide was dissolved in 36 mL methanol; 6.1 mL (10 mol equiv.) iodomethane was added and the reaction mixture was heated at 50° C. for 4 hours. Volatiles were removed under reduced pressure, and the residue was taken up in DCM and extracted with 5% aqueous NaHCO3. The organic layer was washed twice with water, dried over Na2SO4, filtered and evaporated to dryness to yield 1.68 g (87%) 4,N-diethyl-4,5-dihydro-pyrazole-1-carboximidothioic acid methyl ester. 1H NMR (400 MHz, CDCl3) δ 0.98 (t, J=7.5 Hz, 3H), 1.16 (t, J=7.3 Hz, 3H), 1.45-1.70 (m, 2H), 2.45 (s, 3H), 2.97-3.07 (m, 1H), 3.44 (dd, J=11.0, 8.3 Hz, 1H), 3.51-3.58 (m, 2H), 3.83 (t, J=11.0 Hz, 1H), 6.81 (s, 1H).

Workup

  1. customVolatiles were removed under reduced pressure
  2. extractionextracted with 5% aqueous NaHCO3
  3. washThe organic layer was washed twice with water
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-da81e207d7aa416fb749827a5c95220f
Source dataset
uspto-grants-2016_08
Patent number
US09422244B2

Reaction notes

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