Methyl iodide → N'-[amino(methylsulfanyl)methyl]-N,N-dimethylethanimidamide;hydroiodide

HRID 886782Notes

Reaction equation

HRID 886782 reaction equation
[NH2:1][C:2](/[N:4]=[C:5](/[N:7]([CH3:9])[CH3:8])\[CH3:6])=[S:3].[CH3:10][I:11]>C1COCC1>[IH:11].[NH2:1][CH:2]([S:3][CH3:10])/[N:4]=[C:5](/[N:7]([CH3:9])[CH3:8])\[CH3:6]

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 10654343(E)-1-(dimethylamino)ethylidenethiourea

Product 1

HCID 87308795N'-[amino(methylsulfanyl)methyl]-N,N-dimethylethanimidamide;hydroiodideYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A suspension of (1E)-N′-(aminocarbonothioyl)-N,N-dimethylethanimidamide (47.8 g, 0.33 mole) in methyl iodide (150 mL) and THF (350 mL) was stirred for 18 h at room temperature. The mixture was evaporated under reduced pressure. After addition of 5% MeOH and diethyl ether, the compound precipitated and was collected by filtration affording (1E)-N′-[amino(methylthio)methyl]-N,N-dimethylethanimidamide hydrogen iodide salt (91.0 g, 96% yield).

Workup

  1. customThe mixture was evaporated under reduced pressure
  2. additionAfter addition of 5% MeOH and diethyl ether
  3. customthe compound precipitated
  4. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-4b204b1eb3d947308a9bd5164c264b38
Source dataset
uspto-grants-2012_08
Patent number
US08247408B2

Reaction notes

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