Methyl isothiocyanate → HCID 15171119, compound

HRID 1781584Notes

Reaction equation

HRID 1781584 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[CH:4][N:3]=1.[CH3:9][N:10]=[C:11]=[S:12]>C(#N)C>[Cl:1][C:2]1[N:3]=[CH:4][C:5]([NH:8][C:11]([NH:10][CH3:9])=[S:12])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 11167Methyl isothiocyanate2×HCID 793055-Amino-2-chloropyridine

Product 1

HCID 15171119HCID 15171119, compoundYield 70.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 4.07 g of 2-chloro-5-aminopyridine, 2.55 g of methyl isothiocyanate and 30 ml of acetonitrile was refluxed for 13.5 hours, to which 0.70 g of additional methyl isothiocyanate was added and the mixture was refluxed for 3.5 hours. The reaction mixture was concentrated, and the residue was purified by a column chromatography [developing solvent: dichloromethaneethyl acetate (1:1)] to afford 4.51 g of 1-(6-chloro-3-pyridyl)-3-methylthiourea.

Workup

  1. additionwas added
  2. temperaturethe mixture was refluxed for 3.5 hours
  3. concentrationThe reaction mixture was concentrated
  4. customthe residue was purified by a column chromatography [developing solvent: dichloromethaneethyl acetate (1:1)]

Sources & evidence

ORD record
ord-ddec34ddcf93426ea32b4d8fd7bea2af
Source dataset
uspto-grants-1997_05
Patent number
US05633375

Reaction notes

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