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

HRID 1954990Notes

Reaction equation

HRID 1954990 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 crystals. 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 crystals
  4. customThese crystals were recrystallized from AcOEt
  5. washwashed with ether
  6. customdried

Sources & evidence

ORD record
ord-b348e48cc3c04d0790ca9e6b5ebdd71f
Source dataset
uspto-grants-2000_09
Patent number
US06124297

Reaction notes

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