Ethanol → HCID 19025437, compound

HRID 1030971Notes

Reaction equation

HRID 1030971 reaction equation
C(O)C.[Cl:4][C:5]1[CH:10]=[C:9]([N+:11]([O-])=O)[CH:8]=[CH:7][C:6]=1[N:14]1[C:18](=[S:19])[N:17]([CH3:20])[N:16]=[C:15]1[C:21]([F:24])([F:23])[F:22]>Cl.O.[Fe]>[NH2:11][C:9]1[CH:8]=[CH:7][C:6]([N:14]2[C:18](=[S:19])[N:17]([CH3:20])[N:16]=[C:15]2[C:21]([F:23])([F:22])[F:24])=[C:5]([Cl:4])[CH:10]=1

Participants

6

Reactant 2

HCID 702EthanolHCID 19025441HCID 19025441, compound

Product 1

HCID 19025437HCID 19025437, compoundYield 90.1%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

To a stirred mixture of 18.8 g (0.0337 mole) of iron powder in 400 ml of concentrated hydrochloric acid, 20 ml of water, and 300 ml of ethanol was added slowly 28.5 g of 4-(2-chloro-4-nitrophenyl)-3-trifluoromethyl-4,5-dihydro-1-methyl-1,2,4-triazol-5(1H)-thione. This mixture was heated at reflux for eight hours and then was cooled to room temperature and stirred for approximately 18 hours. The mixture was heated to reflux and was filtered hot. The filter cake was washed with methylene chloride. The wash and the filtrate were combined, and the solvents were removed by evaporation under reduced pressure, leaving a residue. This residue was purified by column chromatography on silica gel, eluting with diethyl ether to yield 23.4 g of 4-(4-amino-2-chlorophenyl)-3-trifluoromethyl-4,5-dihydro-1-methyl-1,2,4-triazol-5(1H)-thione as a solid, mp 145°-147° C., Compound 94 of Table 1. The nmr spectrum was consistent with the proposed structure.

Workup

  1. temperatureThis mixture was heated
  2. temperatureat reflux for eight hours
  3. temperatureThe mixture was heated
  4. temperatureto reflux
  5. filtrationwas filtered hot
  6. washThe filter cake was washed with methylene chloride
  7. washThe wash
  8. customthe solvents were removed by evaporation under reduced pressure
  9. customleaving a residue
  10. customThis residue was purified by column chromatography on silica gel
  11. washeluting with diethyl ether

Sources & evidence

ORD record
ord-989a51992314468e8aeb5c30708b03db
Source dataset
uspto-grants-1992_04
Patent number
US05108486

Reaction notes

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