Methyl iodide → HCID 25121369, compound

HRID 1924421Notes

Reaction equation

HRID 1924421 reaction equation
[CH2:1]([N:3]([CH2:17][CH3:18])[C:4](=S)[NH:5][C:6]1[CH:15]=[CH:14][CH:13]=[CH:12][C:7]=1[C:8]([O:10]C)=O)[CH3:2].IC.[C:21]1([CH2:27][C:28]([NH:30][NH2:31])=[O:29])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CO>[CH2:17]([N:3]([CH2:1][CH3:2])[C:4]1[N:31]([NH:30][C:28](=[O:29])[CH2:27][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:8](=[O:10])[C:7]2[C:6](=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:5]=1)[CH3:18]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 70301Benzeneacetic acid, hydrazideHCID 44221300HCID 44221300, compound

Product 1

HCID 25121369HCID 25121369, compoundYield 14%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

Methyl 2-(3,3-diethyl-thioureido)benzoate (0.500 g, 1.88 mmol) was dissolved in methanol (10 mL), followed by addition of iodomethane (234 μL, 3.75 mmol). The reaction mixture was heated at 80° C. for 10 minutes under microwave conditions making sure the temperature did not exceed 80° C. The reaction mixture was evaporated to dryness and then redissolved in ethanol (20 mL), followed by addition of phenylacetic acid hydrazide (0.367 g, 2.44 mmol). The mixture was stirred for 48 h at reflux. After cooling the mixture was filtered and the filtrate was evaporated to dryness. The crude product was purified by column chromatography (EtOAc/Heptane) giving the title compound (0.089 g, 14%). LC-ESI-HRMS of [M+H]+ shows 351,1818 Da. Calc. 351,182101 Da.

Workup

  1. customdid not exceed 80° C
  2. customThe reaction mixture was evaporated to dryness
  3. dissolutionredissolved in ethanol (20 mL)
  4. temperatureat reflux
  5. temperatureAfter cooling the mixture
  6. filtrationwas filtered
  7. customthe filtrate was evaporated to dryness
  8. customThe crude product was purified by column chromatography (EtOAc/Heptane)

Sources & evidence

ORD record
ord-97697b5c5cab4790a797a9a23bdf1678
Source dataset
uspto-grants-2012_05
Patent number
US08178544B2

Reaction notes

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