Methyl iodide → HCID 67360227, compound

HRID 1484439Notes

Reaction equation

HRID 1484439 reaction equation
[CH2:1]([NH:3][C:4]([N:6]1[CH2:10][CH2:9][C:8]([CH2:11][CH3:12])=[N:7]1)=[S:5])[CH3:2].I[CH3:14]>CO>[CH3:14][S:5][C:4]([N:6]1[CH2:10][CH2:9][C:8]([CH2:11][CH3:12])=[N:7]1)=[N:3][CH2:1][CH3:2]

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 86677608HCID 86677608, compound

Product 1

HCID 67360227HCID 67360227, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

1.51 g (1 mol equiv.) 3-Ethyl-4,5-dihydro-pyrazole-1-carbothioic acid ethylamide was dissolved in 30 mL methanol, 5.1 mL (10 mol equiv.) iodomethane was added and the reaction mixture was heated at 50° C. for 1 hour. 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 1.44 g (89%) 3,N-diethyl-4,5-dihydro-pyrazole-1-carboximidothioic acid methyl ester. 1H NMR (400 MHz, CDCl3) δ 1.12-1.21 (m, 6H), 2.39 (q, J=7.4 Hz, 2H), 2.48 (s, 3H), 2.70 (t, J=9.7 Hz, 2H), 3.52 (q, J=7.2 Hz, 2H), 3.75 (t, J=9.7 Hz, 2H).

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-743ea9c5b3284cc98dcc3a5c65b71a27
Source dataset
uspto-grants-2016_08
Patent number
US09422244B2

Reaction notes

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