Acetonitrile → HCID 2085532, compound

HRID 1155745Notes

Reaction equation

HRID 1155745 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:19]=[CH:18][C:17]([OH:20])=[C:16]([CH3:21])[CH:15]=1.C([O-])([O-])=O.[K+].[K+].C(#N)C>O.CC(C)=O>[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][C:2]2[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:3]=2[C:4]#[N:5])=[C:16]([CH3:21])[CH:15]=1

Participants

7

Reactant 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 148554-Chloro-2-methylphenolHCID 855042-Chloro-5-nitrobenzonitrile

Product 1

HCID 2085532HCID 2085532, compoundYield 62.4%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 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 9.73 g (0.0533 moles) of 2-chloro-5-nitrobenzonitrile, 7.83 g (0.0549 moles) of 4-chloro-2-methylphenol, 7.56 g (0.0549 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 then 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 400 ml of absolute ethanol and a small amount of acetone to give 9.60 g (62% yield) of purified 2-(4-chloro-2-methylphenoxy)-5-nitrobenzonitrile, mp 144.5°-145.5° 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 400 ml of absolute ethanol

Sources & evidence

ORD record
ord-66427acef9c944b39040ebe617996791
Source dataset
uspto-grants-1982_06
Patent number
US04332820

Reaction notes

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