Methyl iodide → HCID 178491371, compound

HRID 447918

Reaction equation

HRID 447918 reaction equation
[NH2:1][C:2]([NH:4][C:5]([NH2:7])=[S:6])=S.CI.[CH3:10][O:11][C:12]1[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH3:21])[C:13]=1[CH2:14][NH2:15]>CO.C(O)C>[CH3:21][O:20][C:16]1[CH:17]=[CH:18][CH:19]=[C:12]([O:11][CH3:10])[C:13]=1[CH2:14][NH:15][C:2](=[NH:1])[NH:4][C:5]([NH2:7])=[S:6]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 2758725DithiobiuretHCID 28008722,6-Dimethoxybenzylamine

Product 1

HCID 178491371HCID 178491371, compoundYield 24.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Conditions

Temperature
5 °C

Procedure

2.00 g (14.8 mmol) dithiobiuret were placed in 25 ml methanol and 2.10 g (14.8 mmol) methyliodide were added at room temperature. The mixture was heated for 3 hours at reflux, then the solution was concentrated, was diluted with 25 ml of ethanol and 2.47 g (14.8 mmol) 2,6-dimethoxybenzylamine were added. The mixture was subsequently stirred again for 2 hours at reflux and subsequently for 30 minutes at 5° C. Filtration of the precipitate formed yielded 970 mg N-[[(2,6-dimethoxybenzyl)amino](imino)methyl]thiourea.

Workup

  1. temperatureThe mixture was heated for 3 hours
  2. temperatureat reflux
  3. concentrationthe solution was concentrated
  4. additionwere added
  5. filtrationFiltration of the precipitate
  6. customformed

Sources & evidence

ORD record
ord-6744622eee2342b994d28f4b51c2f171
Source dataset
uspto-grants-2013_07
Patent number
US08481576B2

Linked notes

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