Methyl iodide → HCID 178489511, compound

HRID 447915Notes

Reaction equation

HRID 447915 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[NH:6][C:7]([NH2:9])=S.CI.[CH3:12][O:13][C:14]1[CH:21]=[CH:20][CH:19]=[CH:18][C:15]=1[CH2:16][NH2:17]>CO.C(O)C>[CH3:12][O:13][C:14]1[CH:21]=[CH:20][CH:19]=[CH:18][C:15]=1[CH2:16][NH:17][C:7]([NH:6][C:2]1[S:1][CH:5]=[CH:4][N:3]=1)=[NH:9]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 812922-MethoxybenzylamineHCID 27710081,3-Thiazol-2-ylthiourea

Product 1

HCID 178489511HCID 178489511, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

400 mg (2.51 mmol) N-1,3-thiazole-2-yl-thiourea were suspended in 20 ml of methanol and 392 mg (2.76 mmol) methyl iodide were added. The reaction mixture was stirred for 4 hours at reflux. Following removal of the solvent by vacuum distillation, the residue obtained was dissolved in 20 ml ethanol, 1.72 g (12.6 mmol) 2-methoxybenzylamine were added and the mixture was stirred for 20 hours at reflux. The solvent was removed on the rotovap. The residue was separated by preparative HPLC(RP-18 column, eluent water/acetonitrile/0.1% acetic acid) and 380 mg N-(2-methoxybenzyl)-N′-1,3-thiazole-2-ylguanidine were obtained.

Workup

  1. temperatureat reflux
  2. customremoval of the solvent
  3. distillationby vacuum distillation
  4. customthe residue obtained
  5. stirringthe mixture was stirred for 20 hours
  6. temperatureat reflux
  7. customThe solvent was removed on the rotovap
  8. customThe residue was separated by preparative HPLC(RP-18 column, eluent water/acetonitrile/0.1% acetic acid) and 380 mg N-(2-methoxybenzyl)-N′-1,3-thiazole-2-ylguanidine
  9. customwere obtained

Sources & evidence

ORD record
ord-3fe931c8d63c4fc9b5137f254da77758
Source dataset
uspto-grants-2013_07
Patent number
US08481576B2

Reaction notes

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