Acetonitrile → HCID 12850772, compound

HRID 1155746Notes

Reaction equation

HRID 1155746 reaction equation
Cl[C:2]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:3]=1[C:4]#[N:5].[Cl:13][C:14]1[CH:15]=[C:16]([OH:22])[CH:17]=[C:18]([Cl:21])[C:19]=1[Cl:20].C([O-])([O-])=O.[K+].[K+].C(#N)C>O>[Cl:13][C:14]1[CH:15]=[C:16]([CH:17]=[C:18]([Cl:21])[C:19]=1[Cl:20])[O:22][C:2]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:3]=1[C:4]#[N:5]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 118593,4,5-TrichlorophenolHCID 855042-Chloro-5-nitrobenzonitrile

Product 1

HCID 12850772HCID 12850772, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a 250 ml single-neck flask equipped with a magnetic stirrer and a reflux condenser fitted with a nitrogen bubbler were placed 8.68 g (0.0475 moles) of 2-chloro-5-nitrobenzonitrile 9.67 g (0.0489 moles) of 3,4,5-trichlorophenol, 6.75 g (0.0489 moles) of anhydrous K2CO3, and 75 ml of acetonitrile. The mixture was heated to reflux and held there for 3 hrs. The reaction mixture was cooled to room temperature and diluted with 150 ml of water. The product separated as a solid. The solid was filtered off, washed thoroughly with water, and air-dried. The air-dried solid was recrystallized from a mixture of 200 ml of absolute ethanol and 100 ml of acetone to give 11.62 g (71% yield) of purified 2-(3,4,5-trichlorophenoxy)-5-nitrobenzonitrile as small white crystals, mp 162°-164° C.

Workup

  1. customIn a 250 ml single-neck flask equipped with a magnetic stirrer and a reflux condenser
  2. customfitted with a nitrogen bubbler
  3. temperatureThe mixture was heated
  4. temperatureto reflux
  5. customThe product separated as a solid
  6. filtrationThe solid was filtered off
  7. washwashed thoroughly with water
  8. customair-dried
  9. customThe air-dried solid was recrystallized from a mixture of 200 ml of absolute ethanol and 100 ml of acetone

Sources & evidence

ORD record
ord-a64f8362f39f4b22990b4400f2a38819
Source dataset
uspto-grants-1982_06
Patent number
US04332820

Reaction notes

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