Toluene → N-(6-chloro-3-pyridylmethyl)-N-(2,2,2-trifluoroethyl)-N'-methylthiourea

HRID 1585046Notes

Reaction equation

HRID 1585046 reaction equation
C1(C)C=CC=CC=1.[Cl:8][C:9]1[N:14]=[CH:13][C:12]([CH2:15][NH:16][CH2:17][C:18]([F:21])([F:20])[F:19])=[CH:11][CH:10]=1.[CH3:22][N:23]=[C:24]=[S:25].CCOCC>CCCCCC>[Cl:8][C:9]1[N:14]=[CH:13][C:12]([CH2:15][N:16]([CH2:17][C:18]([F:21])([F:19])[F:20])[C:24]([NH:23][CH3:22])=[S:25])=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 3283Diethyl EtherHCID 11167Methyl isothiocyanateHCID 22450432N-(6-Chloro-3-pyridylmethyl)-N-(2,2,2-trifluoroethyl)amine

Product 1

HCID 22450534N-(6-chloro-3-pyridylmethyl)-N-(2,2,2-trifluoroethyl)-N'-methylthioureaYield 55.3%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent2×

Procedure

In 35 m of toluene, 3,79 g (0.0169 mole) of N-(6-chloro-3-pyridylmethyl)-N-(2,2,2-trifluoroethyl)amine and 2.46 g of methyl isothiocyanate were stirred for 18 hours under reflux. The toluene was distilled off, and the residue was dissolved in 120 m of AcOEt, washed with 1N HC, (two ties) and aqueous sodium chloride solution in this order and dried over MgSO4. The AcOEt was distilled off to give oil. To this oily product were added Et2O and hexane, followed by cooling to give crystals. After addition of hexane to the mixture, the crystals were collected by filtration and dried to give 2.78 g of N-(6-chloro-3-pyridylmethyl)-N-(2,2,2-trifluoroethyl)-N'-methylthiourea as white crystals.

Workup

  1. temperatureunder reflux
  2. distillationThe toluene was distilled off
  3. dissolutionthe residue was dissolved in 120 m of AcOEt
  4. washwashed with 1N HC, (two ties) and aqueous sodium chloride solution in this order
  5. dry with materialdried over MgSO4
  6. distillationThe AcOEt was distilled off
  7. customto give oil
  8. temperatureby cooling
  9. customto give crystals
  10. filtrationthe crystals were collected by filtration
  11. customdried

Sources & evidence

ORD record
ord-4c90277089854a8681247c6327b976ef
Source dataset
uspto-grants-1999_08
Patent number
US05935981

Reaction notes

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