Methyl iodide → Hydrazine

HRID 441683Notes

Reaction equation

HRID 441683 reaction equation
Cl.[CH3:2][CH:3]1[CH2:7][NH:6][C:5]([NH:8][NH2:9])=[N:4]1.CC1CN[C:13](=[S:16])N1.C[I:18]>C(O)C>[IH:18].[CH3:2][CH:3]1[CH2:7][NH:6][C:5]([S:16][CH3:13])=[N:4]1.[NH2:8][NH2:9]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 27773124-Methylimidazolidine-2-thioneHCID 178430663HCID 178430663, compound

Product 2

HCID 9321HydrazineHCID 178503452HCID 178503452, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The starting material, 4-methyl-2-imidazolin-2-ylhydrazine hydrochloride, is prepared as follows: 4-methylimidazolidin-2-thione and methyl iodide react in refluxing ethanol to give 4-methyl-2-methylthio-2-imidazoline hydroiodide, which upon treatment with hydrazine in boiling ethanol yields 4-methyl-2-imidazolin-2-ylhydrazine hydroiodide. Subsequent treatment with silver chloride in aqueous or ethanol solution then gives the hydrochloride salt melting at 128°-130° C.

Sources & evidence

ORD record
ord-aa83b4f6ff5b4025b5a64cfb28aa0e9e
Source dataset
uspto-grants-1977_08
Patent number
USRE029358

Reaction notes

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