Ammonia → HCID 178508669, compound

HRID 1488903Notes

Reaction equation

HRID 1488903 reaction equation
[C:1](#[N:10])[C:2]1[C:3](=[CH:6][CH:7]=[CH:8][CH:9]=1)[C:4]#[N:5].C[O-].[Na+].[NH3:14]>C(O)CCC>[NH:5]=[C:4]1[C:3]2[C:2](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:1](=[NH:14])[NH:10]1

Participants

5

Reactant 3

HCID 222Ammonia2×HCID 7042PhthalonitrileHCID 10942334Sodium Methoxide

Product 1

HCID 178508669HCID 178508669, compoundYield 95.1%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

To 180 mi of n-butanol were fed 21 g (0.06325 mole) of a phthalonitrile represented by the formula (XXI) and 8.54 g (0.1581 mole) of sodium methoxide. The mixture was stirred at room temperature for 1 hour while blowing NH3 gas thereinto and, then, stirred with heating at 70°-80° C. for 3 hours (while blowing NH3 gas). After being cooled to room temperature, n-BuOH was removed by distillation. The concentrate was dissolved in 800 ml of chloroform and was washed well with water and with hot water. Water in the organic layer was removed with magnesium sulfate and chloroform was removed by distillation. The residue was recrystallized from hexane to obtain 21 g (yield: 95.1%) of a compound having the following formula (XXII). The compound is in the form of light yellow crystals and shows no melting point and a decomposition point of 205° C. The IR spectrum of this compound is shown in FIG. 8. ##STR53##

Workup

  1. stirringstirred
  2. temperatureAfter being cooled to room temperature
  3. customn-BuOH was removed by distillation
  4. dissolutionThe concentrate was dissolved in 800 ml of chloroform
  5. washwas washed well with water and with hot water
  6. customWater in the organic layer was removed with magnesium sulfate and chloroform
  7. customwas removed by distillation
  8. customThe residue was recrystallized from hexane

Sources & evidence

ORD record
ord-25f4029480bc4652a4f1720ad38c95d6
Source dataset
uspto-grants-1997_10
Patent number
US05677025

Reaction notes

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