Thiourea → HCID 178526654, compound

HRID 402340Notes

Reaction equation

HRID 402340 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([C:11]([F:14])([F:13])[F:12])=[CH:4][N:3]=1.NC(N)=[S:17]>C(O)C>[N+:8]([C:7]1[C:2]([SH:17])=[N:3][CH:4]=[C:5]([C:11]([F:14])([F:13])[F:12])[CH:6]=1)([O-:10])=[O:9]

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 47369502-Chloro-3-nitro-5-(trifluoromethyl)pyridine

Product 1

HCID 178526654HCID 178526654, compoundYield 79.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 4.88 g of 2-chloro3-nitro-5-(trifluoromethyl)pyridine, 1.81 g of thiourea and 40 ml of ethanol was stirred at 50° C. for 5.5 hours. The reaction mixture was cooled down to room temperature, then, concentrated under reduced pressure. To the residue was added 24 ml of water and a mixture of 2.8 g of sodium hydroxide and 6 ml of water, and this was stirred at room temperature for 1.5 hours. The reaction mixture was washed with diethyl ether, then, acetic acid was added. This was cooled with ice, and the deposited solid was collected by filtration. This solid was dried under reduced pressure, to obtain 3.84 g of 3-nitro-5-(trifluoromethyl)pyridine-2-thiol.

Workup

  1. temperatureThe reaction mixture was cooled down to room temperature
  2. concentrationconcentrated under reduced pressure
  3. additionTo the residue was added 24 ml of water
  4. additiona mixture of 2.8 g of sodium hydroxide and 6 ml of water
  5. stirringthis was stirred at room temperature for 1.5 hours
  6. washThe reaction mixture was washed with diethyl ether
  7. additionacetic acid was added
  8. temperatureThis was cooled with ice
  9. filtrationthe deposited solid was collected by filtration
  10. customThis solid was dried under reduced pressure

Sources & evidence

ORD record
ord-f690258d91474877a5abf82723a8015d
Source dataset
uspto-grants-2014_06
Patent number
US08742112B2

Reaction notes

Loading…