HCID 22450431, compound → Methyl(2-pyridylmethyl)amine

HRID 1954984Notes

Reaction equation

HRID 1954984 reaction equation
CSC(=NC)[N:4]([CH2:6][C:7]1[CH:12]=[CH:11][C:10](Cl)=[CH:9]C=1)[CH3:5].C[NH:17]C(N(C)CC1C=CN=CC=1)=S>[N+](C)([O-])=O>[CH3:5][NH:4][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][N:17]=1

Participants

4

Reactant 2

HCID 22450431HCID 22450431, compoundHCID 22450450HCID 22450450, compound

Product 1

HCID 88757Methyl(2-pyridylmethyl)amine

Reagents, catalysts & solvents 1

HCID 6375NitromethaneSolvent

Procedure

To 4.98 g (0.0205 mole) of S-methyl-N-(4-chlorobenzyl)-N-methyl-N'-methylisothiourea prepared in (1) was added 25 ml of nitromethane and the mixture was refluxed for 6.5 hours. The nitromethane was distilled off and the residue was subjected to silica gel (240 g) column chromatography using MeOH--CHCl3 (1:10) as an eluent to give 5.23 g of an orange-colored oil. To this oil were added small amounts of EtOH and ether and the mixture was cooled in a dry ice-acetone bath and triturated to give crystals. After addition of ether, the crystals were collected by filtration, washed with ether and dried. The procedure gave 3.69 g of the title compound as pale yellow cyrstals.

Workup

  1. temperaturethe mixture was refluxed for 6.5 hours
  2. distillationThe nitromethane was distilled off

Sources & evidence

ORD record
ord-4a00f573b92c47dd8b3670ac44ff43a1
Source dataset
uspto-grants-2000_09
Patent number
US06124297

Reaction notes

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