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

HRID 1954996Notes

Reaction equation

HRID 1954996 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][NH:9][CH2:10][C:11]([F:14])([F:13])[F:12])=[CH:4][CH:3]=1.[CH3:15][N:16]=[C:17]=[S:18].CCOCC.CCCCCC>C1(C)C=CC=CC=1>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][N:9]([CH2:10][C:11]([F:14])([F:12])[F:13])[C:17]([NH:16][CH3:15])=[S:18])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 8058Hexane2×HCID 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 1140TolueneSolvent

Procedure

In 35 ml 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 ml of AcOEt, washed with 1N HCl (two times) 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 ml of AcOEt
  4. washwashed with 1N HCl (two times) 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-b4abf2ef56be4b11a0c0a678bcfa1ad4
Source dataset
uspto-grants-2000_09
Patent number
US06124297

Reaction notes

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