Ammonium Chloride → 4-(2-Chloro-4-methyl-thiazol-5-yl)-phenylamine

HRID 908155Notes

Reaction equation

HRID 908155 reaction equation
[In].[Cl-].[NH4+].[Cl:4][C:5]1[S:6][C:7]([C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[CH:13][CH:12]=2)=[C:8]([CH3:10])[N:9]=1>C(O)C.Cl>[Cl:4][C:5]1[S:6][C:7]([C:11]2[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][CH:12]=2)=[C:8]([CH3:10])[N:9]=1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 5359967IndiumHCID 673914002-Chloro-4-methyl-5-(4-nitro-phenyl)-thiazole

Product 1

HCID 673917684-(2-Chloro-4-methyl-thiazol-5-yl)-phenylamineYield 96.3%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

Indium powder (0.64 mg, 2.5 mmol) and saturated ammonium chloride solution (3 ml, 2.5 mmol) are added to a solution of 2-chloro-4-methyl-5-(4-nitro-phenyl)-thiazole (25b) (0.20 g, 0.786 mmol) in ethanol (3 ml). The mixture is heated at reflux with stirring for 90 minutes. When cool the mixture is diluted with 2M aqueous hydrochloric acid to dissolve any product and the mixture is filtered through celite. The filtrate is adjusted to pH 9 with aqueous sodium hydroxide and extracted with dichloromethane (3×30 ml). The combined organic extract is dried (MgSO4) filtered, and the solvent removed to give the title compound as a yellow solid (0.17 g).

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux
  3. temperatureWhen cool the mixture
  4. dissolutionto dissolve any product
  5. filtrationthe mixture is filtered through celite
  6. extractionextracted with dichloromethane (3×30 ml)
  7. extractionThe combined organic extract
  8. dry with materialis dried (MgSO4)
  9. filtrationfiltered
  10. customthe solvent removed

Sources & evidence

ORD record
ord-6a59d023ea91412f9aa4dbefe8b686e8
Source dataset
uspto-grants-2011_09
Patent number
US08017608B2

Reaction notes

Loading…