Ethanol → HCID 21439838, compound

HRID 328710Notes

Reaction equation

HRID 328710 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.Cl[C:10]1[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][C:11]=1[NH2:12].[OH-].[K+].C(O)C>O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:10]2[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][C:11]=2[NH2:12])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 14797Potassium HydroxideHCID 226912-Chloro-5-nitroanilineHCID 677894-Fluorothiophenol

Product 1

HCID 21439838HCID 21439838, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 29.7 g. (0.231 mole) of 4-fluorothiophenol, 41 g. (0.238 mole) of 2-chloro-5-nitroaniline and 14.9 g. (0.266 mole) of potassium hydroxide in 500 ml. of 95 percent aqueous ethanol is heated to its reflux temperature and maintained at reflux for one hour, then cooled with an ice bath. Some crude product is isolated as a solid by filtration, then the filtrate is diluted with water and extracted with four 300 ml. portions of chloroform. The combined extracts are washed with four 300 ml. portions of water and then with saturated sodium chloride solution and dried. Evaporation under vacuum provides a residue which is combined with the previously isolated crude solid product, 2-(4-fluorophenylthio)-5-nitroaniline. The solid is dissolved in 500 ml. of chloroform, then the solution is saturated with hydrogen chloride gas. The white precipitate which forms is separated by filtration, washed with chloroform and diethyl ether and dried to provide 2-(4-fluorophenylthio)-5-nitroaniline hydrochloride.

Workup

  1. additionA mixture of 29.7 g
  2. temperaturereflux temperature
  3. temperaturemaintained
  4. temperatureat reflux for one hour
  5. temperaturecooled with an ice bath
  6. customSome crude product is isolated as a solid by filtration
  7. extractionextracted with four 300 ml
  8. washThe combined extracts are washed with four 300 ml
  9. dry with materialportions of water and then with saturated sodium chloride solution and dried
  10. customEvaporation under vacuum
  11. customprovides a residue which

Sources & evidence

ORD record
ord-07e73dd9167f4dfdb801134d356dbb40
Source dataset
uspto-grants-1977_04
Patent number
US04018780

Reaction notes

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