Methyl iodide → HCID 67360167, compound

HRID 1484446Notes

Reaction equation

HRID 1484446 reaction equation
[CH2:1]([NH:3][C:4]([N:6]1[CH:10]([C:11]2[CH:15]=[CH:14][S:13][CH:12]=2)[CH2:9][CH:8]=[N:7]1)=[S:5])[CH3:2].I[CH3:17]>CO>[CH3:17][S:5][C:4]([N:6]1[CH:10]([C:11]2[CH:15]=[CH:14][S:13][CH:12]=2)[CH2:9][CH:8]=[N:7]1)=[N:3][CH2:1][CH3:2]

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 86677609HCID 86677609, compound

Product 1

HCID 67360167HCID 67360167, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

0.70 g (1 mol equiv.) 5-Thiophen-3-yl-4,5-dihydro-pyrazole-1-carbothioic acid ethylamide was dissolved in 14 mL methanol, 1.82 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 dichloromethane and extracted with 5% aqueous NaHCO3. The organic layer was washed twice with water, dried over Na2SO4, filtered and evaporated to dryness. Purification by flash chromatography on silica gel (EtOAc:MeOH=9:1) afforded 0.48 g (64%) N-ethyl-5-thiophen-3-yl-4,5-dihydro-pyrazole-1-carboximidothioic acid methyl ester. 1H NMR (400 MHz, CDCl3) δ 1.03 (t, J=7.3, 3H), 2.44 (s, 3H), 2.84 (ddd, J=18.1, 10.4, 1.5 Hz, 1H), 3.23-3.51 (m, 3H), 5.57 (t, J=10.4 Hz, 1H), 6.87 (br.s., 1H), 7.00 (d, J=4.8, 1H), 7.13 (d, J=3.0, 1H), 7.24 (dd, J=4.8, 3.0 Hz, 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
  7. customPurification by flash chromatography on silica gel (EtOAc:MeOH=9:1)

Sources & evidence

ORD record
ord-81356a6063344ebbbf1e4e5900a23210
Source dataset
uspto-grants-2016_08
Patent number
US09422244B2

Reaction notes

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