Bromine → 2-[Bromo(nitro)methylidene]-1-methylimidazolidine

HRID 1414899Notes

Reaction equation

HRID 1414899 reaction equation
[CH3:1][N:2]1[CH2:6][CH2:5][NH:4][C:3]1=[CH:7][N+:8]([O-:10])=[O:9].[Br:11]Br>O>[Br:11][C:7]([N+:8]([O-:10])=[O:9])=[C:3]1[NH:4][CH2:5][CH2:6][N:2]1[CH3:1]

Participants

4

Reactant 2

HCID 24408BromineHCID 702500461-Methyl-2-(nitromethylidene)imidazolidine2×

Product 1

HCID 706389552-[Bromo(nitro)methylidene]-1-methylimidazolidine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A stirred solution of 3.57 grams of 1-methyl-2-(nitromethylene)imidazolidine (Compound 1) in 25 milliliters of water was treated dropwise with 3.99 grams of bromine at room temperature. After 30 minutes, the reaction mixture was extracted with methylene chloride. The extract was dried (MgSO4) and the solvent was evaporated to give 3.0 grams of crude product, melting point 100° (with vigorous decomposition). Recrystallization of the crude product from methylene chloride gave 15, melting point: 97° (explodes).

Workup

  1. extractionthe reaction mixture was extracted with methylene chloride
  2. dry with materialThe extract was dried (MgSO4)
  3. customthe solvent was evaporated
  4. customto give 3.0 grams of crude product, melting point 100° (with vigorous decomposition)
  5. customRecrystallization of the crude product from methylene chloride

Sources & evidence

ORD record
ord-7e03460326854d94987b1724353d4b8f
Source dataset
uspto-grants-1977_01
Patent number
US04002765

Reaction notes

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