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

HRID 918040Notes

Reaction equation

HRID 918040 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-aba6bbb82a6a497eb5fecfac18c2958d
Source dataset
uspto-grants-1976_07
Patent number
US03969354

Reaction notes

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