Methyl iodide → HCID 67359253, compound

HRID 1484436Notes

Reaction equation

HRID 1484436 reaction equation
[CH2:1]([NH:3][C:4]([N:6]1[CH2:10][C:9]([CH3:12])([CH3:11])[CH:8]=[N:7]1)=[S:5])[CH3:2].I[CH3:14]>CO>[CH3:14][S:5][C:4]([N:6]1[CH2:10][C:9]([CH3:11])([CH3:12])[CH:8]=[N:7]1)=[N:3][CH2:1][CH3:2]

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 866776074,4-Dimethyl-4,5-dihydro-pyrazole-1-carbothioic acid ethylamide

Product 1

HCID 67359253HCID 67359253, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

15 g (1 mol equiv.) 4,4-Dimethyl-4,5-dihydro-pyrazole-1-carbothioic acid ethylamide was dissolved in 300 mL methanol, 50.4 mL (10 mol equiv.) iodomethane was added and the reaction mixture was heated at 50° C. for 3 hours. Volatiles were removed in vacuo. 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 give 15.5 g (96%) N-ethyl-4,4-dimethyl-4,5-dihydro-pyrazole-1-carboximidothioic acid methyl ester. 1H NMR (400 MHz, CDCl3) δ 1.16 (t, J=7.3 Hz, 3H), 1.20 (s, 6H), 2.45 (s, 3H), 3.49 (s, 2H), 3.53 (q, J=7.3 Hz, 2H), 6.66 (s, 1H).

Workup

  1. customVolatiles were removed in vacuo
  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-eb1007df0767492d992342ed921f163e
Source dataset
uspto-grants-2016_08
Patent number
US09422244B2

Reaction notes

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