Ethyl Bromide → Hydrazine

HRID 441682Notes

Reaction equation

HRID 441682 reaction equation
Br.[C:2]1(C2(C3C=CC=CC=3)NC([NH:13][NH2:14])=NC2)C=CC=C[CH:3]=1.[C:21]1([C:27]2([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[CH2:31][NH:30][C:29](=[S:32])[NH:28]2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C([Br:41])C>C(O)C>[BrH:41].[C:33]1([C:27]2([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[NH:28][C:29]([S:32][CH2:2][CH3:3])=[N:30][CH2:31]2)[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1.[NH2:13][NH2:14]

Participants

6

Reactant 3

HCID 6332Ethyl BromideHCID 40059884,4-Diphenylimidazolidine-2-thioneHCID 70636826HCID 70636826, compound

Product 2

HCID 9321HydrazineHCID 70637439HCID 70637439, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The starting material, 5,5-diphenyl-2-imidazolin-2-ylhydrazine hydrobromide, is prepared as follows: 4,4-diphenylimidazolin-2-thione, prepared by the method of Marshall, J. Am. Chem. Soc. 78 3696 (1956), is treated with ethyl bromide in refluxing ethanol to yield 5,5-diphenyl-2-ethylthio-2-imidazoline hydrobromide, which upon treatment with hydrazine in refluxing ethanol gives the desired intermediate, melting point 227°-⟦8°⟧228° C.

Sources & evidence

ORD record
ord-72692aee390747819bfe3052b9e50d6e
Source dataset
uspto-grants-1977_08
Patent number
USRE029358

Reaction notes

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