Methyl isothiocyanate → HCID 15171119, compound

HRID 1087096Notes

Reaction equation

HRID 1087096 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 4.07g of 2-chloro-5-aminopyridine, 2.55g of methyl isothiocyanate and 30ml of acetonitrile was refluxed for 13.5 hours, to which 0.70g 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 4.51g 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-fb34a7d6c70445faa37dc0e9a1acc79e
Source dataset
uspto-grants-1991_07
Patent number
US05034404

Reaction notes

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