Dimethylamine → 1-(6-Chloro-3-pyridylmethyl)amino-1-dimethylamino-2-nitroethylene

HRID 2380093Notes

Reaction equation

HRID 2380093 reaction equation
Cl[C:2](Cl)(Cl)[CH2:3][N+:4]([O-:6])=[O:5].[CH2:9]([N:11](CC)[CH2:12]C)C.CNC.[Cl:19][C:20]1[N:25]=[CH:24][C:23]([CH2:26][NH2:27])=[CH:22][CH:21]=1>O1CCCC1>[Cl:19][C:20]1[N:25]=[CH:24][C:23]([CH2:26][NH:27][C:2]([N:11]([CH3:12])[CH3:9])=[CH:3][N+:4]([O-:6])=[O:5])=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 674DimethylamineHCID 8471Triethylamine2×HCID 70209275-(Aminomethyl)-2-chloropyridineHCID 109541031,1,1-Trichloro-2-nitroethane

Product 1

HCID 598965901-(6-Chloro-3-pyridylmethyl)amino-1-dimethylamino-2-nitroethyleneYield 81.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
0 °C

Procedure

To a solution of 2.10 g (0.0118 mol) of 1,1,1-trichloro-2-nitroethane in 30 ml of tetrahydrofuran was dropwise added a solution of 1.2 g (0.0118 mol) of triethylamine in 2 ml of tetrahydrofuran under cooling to 0° C. and with stirring. To the mixture which was stirred for 30 minutes was dropwise added a solution of 0.99 g (0.011 mol) of 50% dimethylamine and 2.4 g (0.0237 mol) of triethylamine in 5 ml of tetrahydrofuran at -43° C.--38° C. The mixture was stirred for 30 minutes at the same temperature and 1.0 g (0.007 mol) of 6-chloro-3-pyridylmethylamine was dropwise added. The mixture was allowed to stand until rising to room temperature, stirred for 30 minutes and then filtered. The filtrate was concentrated, and 1,2-dichloroethane was added to the residue. The mixture was again filtered to remove insoluble substance. The filtrate was concentrated and the residue was purified by silica gel column chromatography using acetone to obtain 1.46 g (81.0%) of 1-(6-chloro-3-pyridylmethyl)amino-1-dimethylamino- 2-nitroethylene as yellow crystals. mp. 124°-125° C.

Workup

  1. stirringTo the mixture which was stirred for 30 minutes
  2. additionwas dropwise added
  3. customuntil rising to room temperature
  4. stirringstirred for 30 minutes
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated
  7. addition1,2-dichloroethane was added to the residue
  8. filtrationThe mixture was again filtered
  9. customto remove insoluble substance
  10. concentrationThe filtrate was concentrated
  11. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-4ba5ee2e0a6e4f1a8dea818a7d385c56
Source dataset
uspto-grants-1994_11
Patent number
US05364989

Reaction notes

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