4-Methylbenzylamine → HCID 86733218, compound

HRID 1605173Notes

Reaction equation

HRID 1605173 reaction equation
[IH:1].[CH3:2][NH:3][C:4](=[N:7][CH3:8])SC.[CH3:9][C:10]1[CH:17]=[CH:16][C:13]([CH2:14][NH2:15])=[CH:12][CH:11]=1>C(O)C>[IH:1].[CH3:9][C:10]1[CH:17]=[CH:16][C:13]([CH2:14][NH:15][C:4]([NH:7][CH3:8])=[N:3][CH3:2])=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 660354-MethylbenzylamineHCID 2775205Methyl N,N'-dimethylcarbamimidothioate--hydrogen iodide (1/1)

Product 1

HCID 86733218HCID 86733218, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of N,N',S-trimethylisothiourea hydriodide, m.p. 208° -212° (9.84 g.) and p-methyl-benzylamine (4.84 g.) in ethanol (10 ml.) was refluxed for 31/2 hours, filtered, and refluxed for a further 21/2 hours. The solution was then concentrated, and the solid that separated was collected and crystallised from methanol-ethanol to give N-p-methylbenzyl-N', N"-dimethyl-guanidine hydriodide, m.p. 204° - 207°. Recrystallised from water, the m.p. rose to 209° - 212°.

Workup

  1. filtrationfiltered
  2. temperaturerefluxed for a further 21/2 hours
  3. concentrationThe solution was then concentrated
  4. customthe solid that separated
  5. customwas collected
  6. customcrystallised from methanol-ethanol

Sources & evidence

ORD record
ord-d369edb96d9d462aab876c723eef0880
Source dataset
uspto-grants-1976_04
Patent number
US03949089

Reaction notes

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