Dimethylformamide → HCID 53761630, compound

HRID 1033544Notes

Reaction equation

HRID 1033544 reaction equation
[CH:1]([CH:3]=[CH:4][N:5]1[CH2:9][CH2:8][NH:7][C:6]1=[N:10][N+:11]([O-:13])=[O:12])=[O:2].[H-].[Na+].CN(C=O)C.[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([CH2:28]Cl)=[CH:24][N:23]=1>O>[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([CH2:28][N:7]2[CH2:8][CH2:9][N:5]([CH:4]=[CH:3][CH:1]=[O:2])[C:6]2=[N:10][N+:11]([O-:13])=[O:12])=[CH:24][N:23]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 1554792-Chloro-5-(chloromethyl)pyridineHCID 136378394HCID 136378394, compound

Product 1

HCID 53761630HCID 53761630, compoundYield 45.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

A mixture comprising 3.0 g of 1-(formylvinyl)-2-nitroiminoimidazolidine, 0.7 g of sodium hydride and 30 ml of DMF was stirred at 40° C. for 15 minutes. After this was cooled to room temperature, 3.2 g of 2-chloro-5-chloromethylpyridine was added thereto and stirred at 60° C for 2 hours. The reaction mixture was poured into water, extracted with ethyl acetate, washed with water, dried (with anhydrous MgSO4) and concentrated to give an oily residue. This was purified by column chromatography (silica gel, eluent: ethyl acetate) to give 2.3 g of 1-(2-chloropyridin-5-ylmethyl)-2-nitroimino-3-(2-formylvinyl)imidazolidine.

Workup

  1. temperatureAfter this was cooled to room temperature
  2. stirringstirred at 60° C for 2 hours
  3. extractionextracted with ethyl acetate
  4. washwashed with water
  5. dry with materialdried (with anhydrous MgSO4)
  6. concentrationconcentrated
  7. customto give an oily residue
  8. customThis was purified by column chromatography (silica gel, eluent: ethyl acetate)

Sources & evidence

ORD record
ord-6bc439ff85bf4022a521a6afaadb9d8c
Source dataset
uspto-grants-1994_05
Patent number
US05310920

Reaction notes

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