5-Amino-2-chloropyridine → HCID 85593012, compound

HRID 1585040Notes

Reaction equation

HRID 1585040 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:8])=[N:6][CH:7]=1.[CH3:9][S:10][C:11](SC)=[CH:12][N+:13]([O-:15])=[O:14]>C(C1C=CC=CC=1)C>[Cl:8][C:5]1[N:6]=[CH:7][C:2]([NH:1][C:11]([S:10][CH3:9])=[CH:12][N+:13]([O-:15])=[O:14])=[CH:3][CH:4]=1

Participants

4

Reactant 2

HCID 793055-Amino-2-chloropyridineHCID 836231,1-Bis(methylthio)-2-nitroethylene

Product 1

HCID 85593012HCID 85593012, compoundYield 6.7%

Reagents, catalysts & solvents 1

HCID 7500EthylbenzeneSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 3.9 g (0.0303 mole) of 5-amino-2-chloropyridine, 5.0 g of 1,1-bis(methylthio)-2-nitroethylene and 80 ml of ethylbenzene was heated at 130° C. for 2 hours. The ethylbenzene was distilled off under reduced pressure and the crystalline residue was washed with AcOEt and subjected to silica gel column chromatography using EtOH-CHCl3 (1:30) as the eluent to recover crude crystal. These crystals were recrystallized from AcOEt, washed with ether and dried. The procedure gave 0.5 g of 1-(6-chloro-3-pyridyl)amino-1-methylthio-2-nitroethylene as pale yellow crystals.

Workup

  1. distillationThe ethylbenzene was distilled off under reduced pressure
  2. washthe crystalline residue was washed with AcOEt
  3. customto recover crude crystal
  4. customThese crystals were recrystallized from AcOEt
  5. washwashed with ether
  6. customdried

Sources & evidence

ORD record
ord-18c33820700c4e0197b28fa4ae6188ea
Source dataset
uspto-grants-1999_08
Patent number
US05935981

Reaction notes

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