Ammonium Chloride → HCID 19771126, compound

HRID 1589865Notes

Reaction equation

HRID 1589865 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:21])=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:10]=2[N+:18]([O-])=O)[CH:7]=1.[Cl-].[NH4+].O.O.O.O.O.O.O.O.O.[Na+].[SH-]>CO>[ClH:1].[NH2:18][C:10]1[CH:11]=[C:12]([N+:15]([O-:17])=[O:16])[CH:13]=[CH:14][C:9]=1[NH:8][C:6]1[CH:7]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=1[OH:21]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 53601534-Chloro-2-(2,4-dinitroanilino)phenolHCID 23719467HCID 23719467, compound

Product 1

HCID 19771126HCID 19771126, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of N-(5-chloro-2-hydroxyphenyl)-2,4-dinitroaniline (7.9 g, 25.6 mmol), ammoniumchloride (5,2 g, 98 mmol) and sodiumsulfide nonahydrate (23.5 g, 98 mmol) in methanol (350 ml; was refluxed for one hour. The reaction was filtered after cooling to room temperature and the filtrate was concentrated in vacuo. The remanecens was dissolved in ethanol, acidified with concentrated hydrochloric acid and the mixture was concentrated in vacuo. Finally the crude product was triturated with diethyl ether yielding the title compound as red/brown crystals. The product was used without further purification.

Workup

  1. temperaturewas refluxed for one hour
  2. filtrationThe reaction was filtered
  3. concentrationthe filtrate was concentrated in vacuo
  4. dissolutionThe remanecens was dissolved in ethanol
  5. concentrationthe mixture was concentrated in vacuo
  6. customFinally the crude product was triturated with diethyl ether yielding the title compound as red/brown crystals
  7. customThe product was used without further purification

Sources & evidence

ORD record
ord-18db94efdaa0470a8c12822ee559e091
Source dataset
uspto-grants-1993_04
Patent number
US05200422

Reaction notes

Loading…