Pyridine → HCID 22349970, compound

HRID 64107Notes

Reaction equation

HRID 64107 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([N:13]2[CH:17]=[CH:16][CH:15]=[CH:14]2)[CH:7]=[C:8]([N+:10]([O-:12])=[O:11])[CH:9]=1)([O-])=O.N1C=CC=CC=1.[NH4+]=S>C(O)C.O>[N+:10]([C:8]1[CH:9]=[C:4]([NH2:1])[CH:5]=[C:6]([N:13]2[CH:14]=[CH:15][CH:16]=[CH:17]2)[CH:7]=1)([O-:12])=[O:11]

Participants

5

Reactant 2

HCID 1049PyridineHCID 173821411-(3,5-Dinitrophenyl)pyrrole

Product 1

HCID 22349970HCID 22349970, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 1-(3,5-dinitro-phenyl)-1H-pyrrole (8.2 g, 35.19 mmol) and pyridine (10 ml) in ethanol (100 ml), at 80° C., was added a 20% aqueous solution of ammonium sulfide (38.4 ml, 140.76 mmol, 4.0 eq.) in water (10 ml). The mixture was stirred at the same temperature for 4 h. The mixture was quenched with ice water (200 ml) and the precipitated solid was filtered. The filtered solid was dried under vacuum to afford the product in 98% yield (7.0 g).

Workup

  1. customThe mixture was quenched with ice water (200 ml)
  2. filtrationthe precipitated solid was filtered
  3. customThe filtered solid was dried under vacuum
  4. customto afford the product in 98% yield (7.0 g)

Sources & evidence

ORD record
ord-018972639672440ca469b7265fe4d504
Source dataset
uspto-grants-2016_09
Patent number
US09447091B2

Reaction notes

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