Water → N-(3-(1-Imidazolyl)phenyl)-2-amino-4-(3-furanyl)aniline

HRID 581944Notes

Reaction equation

HRID 581944 reaction equation
[N:1]1([C:6]2[CH:7]=[C:8]([NH:12][C:13]3[CH:18]=[CH:17][C:16](C4OC=CC=4)=[CH:15][C:14]=3[N+:24]([O-])=O)[CH:9]=[CH:10][CH:11]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.[Cl-].[NH4+].[OH2:29].O.O.O.O.O.O.O.O.[S-2].[Na+].[Na+].O>C(O)C>[N:1]1([C:6]2[CH:7]=[C:8]([NH:12][C:13]3[CH:18]=[CH:17][C:16]([C:6]4[CH:11]=[CH:10][O:29][CH:7]=4)=[CH:15][C:14]=3[NH2:24])[CH:9]=[CH:10][CH:11]=2)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 73972Sodium sulfide nonahydrateHCID 54198063HCID 54198063, compound

Product 1

HCID 15521704N-(3-(1-Imidazolyl)phenyl)-2-amino-4-(3-furanyl)anilineYield 146.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 7c from Example 11 (13 g, 37.6 mmol) in ethanol (25 ml) is added ammonium chloride (6.03 g, 113 mmol) and sodium sulfide nonahydrate (27.05 g, 113 mmol). The mixture is heated to reflux for 1 hour. After cooling the mixture is poured into 700 ml of water. The product is filtered off, washed with water and air-dried to yield 8c (8.7 g, 73%). Mp 188-189° C.

Workup

  1. temperatureThe mixture is heated
  2. temperatureto reflux for 1 hour
  3. temperatureAfter cooling the mixture
  4. filtrationThe product is filtered off
  5. washwashed with water
  6. customair-dried

Sources & evidence

ORD record
ord-316d9a20b23b413c9475cf406668694f
Source dataset
uspto-grants-1999_07
Patent number
US05922724

Reaction notes

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