Methyl iodide → 4,4-Dimethyl-4,5-dihydro-pyrazole-1-carboximidothioic acid methyl ester

HRID 1484459Notes

Reaction equation

HRID 1484459 reaction equation
[CH3:1][C:2]1([CH3:10])[CH2:6][N:5]([C:7](=[S:9])[NH2:8])[N:4]=[CH:3]1.I[CH3:12]>CO>[CH3:12][S:9][C:7]([N:5]1[CH2:6][C:2]([CH3:10])([CH3:1])[CH:3]=[N:4]1)=[NH:8]

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 866776124,4-Dimethyl-4,5-dihydro-pyrazole-1-carbothioic acid amide

Product 1

HCID 673594724,4-Dimethyl-4,5-dihydro-pyrazole-1-carboximidothioic acid methyl esterYield 94%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1.50 g (1 mol equiv.) 4,4-Dimethyl-4,5-dihydro-pyrazole-1-carbothioic acid amide was dissolved in 30 ml methanol; 5.9 mL (10 mol equiv.) iodomethane was added and the reaction mixture was stirred at room temperature for 2 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, yielding 1.53 g (94%) 4,4-dimethyl-4,5-dihydro-pyrazole-1-carboximidothioic acid methyl ester. 1H NMR (400 MHz, CDCl3) δ 1.24 (s, 6H), 2.32 (s, 3H), 3.65 (s, 2H), 6.63 (s, 1H), 6.66-6.85 (br.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-cf9fa18c11be4371b0f8af1b3cea83c7
Source dataset
uspto-grants-2016_08
Patent number
US09422244B2

Reaction notes

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