Hydrochloric Acid → HCID 21568991, compound

HRID 1579616Notes

Reaction equation

HRID 1579616 reaction equation
N[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.Cl.N([O-])=O.[Na+].[O:15]1[CH:19]=[CH:18][CH:17]=[C:16]1[C:20]([CH3:22])=[O:21]>O.C(#N)C>[C:20]([C:16]1[O:15][C:19]([C:2]2[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=2)=[CH:18][CH:17]=1)(=[O:21])[CH3:22]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 133964-AminobenzonitrileHCID 145052-AcetylfuranHCID 23668193Sodium Nitrite

Product 1

HCID 21568991HCID 21568991, compoundYield 18%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent3×HCID 6342AcetonitrileSolvent

Procedure

A mixture of 50 g (0.42 mole) of p-aminobenzonitrile, 146 ml of concentrated hydrochloric acid, and 106 ml of H2O was heated at 80° for for 20 minutes and then cooled to 0°. A solution of 29 g (0.42 mole) of sodium nitrite in 105 ml of H2O was added dropwise while maintaining the temperature at 0°-5° by means of an ice bath. The reaction was kept at 0° for 45 minutes. A solution of 47 g (0.42 mole) of methyl 2-furyl ketone in 43 ml of acetonitrile was added followed by a solution of 10 g of CuCl2 .2H2O in 50 ml of water. The reaction became exothermic and was controlled below 40°. The reaction was allowed to stand overnight. The aqueous layer was decanted and the residual semisolid was extracted with 6000 ml of refluxing hexane. The hexane was cooled and the resulting precipitate was filtered and air dried to yield 16 g (18%) of p-(5-acetyl-2-furyl)benzonitrile. An analytical sample was prepared by recrystallizing a sample from hexane/charcoal, m.p. 115°-116°.

Workup

  1. temperaturewas heated at 80° for for 20 minutes
  2. temperaturecooled to 0°
  3. temperaturewhile maintaining the temperature at 0°-5° by means of an ice bath
  4. customwas controlled below 40°
  5. waitto stand overnight
  6. customThe aqueous layer was decanted
  7. extractionthe residual semisolid was extracted with 6000 ml of refluxing hexane
  8. temperatureThe hexane was cooled
  9. filtrationthe resulting precipitate was filtered
  10. customair dried

Sources & evidence

ORD record
ord-f804d499dfef4a7c9a734d34a00fa341
Source dataset
uspto-grants-1976_01
Patent number
US03931247

Reaction notes

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