Acetonitrile → Phthalonitrile

HRID 240206

Reaction equation

HRID 240206 reaction equation
[NH2:1][C:2]1[C:3](S(O)(=O)=O)=[CH:4][CH:5]=[C:6](S(O)(=O)=O)[CH:7]=1.[C:16](#[N:18])[CH3:17]>O>[C:2](#[N:1])[C:7]1[C:17](=[CH:3][CH:4]=[CH:5][CH:6]=1)[C:16]#[N:18]

Participants

4

Reactant 2

HCID 6342AcetonitrileHCID 609882-Amino-p-benzenedisulfonic acid

Product 1

HCID 7042Phthalonitrile

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

A solution of aniline 2,5 disulphonic acid (27.5 g) in water (250 ml) was added to intermediate E (63.2 g) in acetonitrile (800 ml) and heated at 40° C. and at pH 5 to 7 overnight. The reaction solvent was removed under reduced pressure, water (50 ml) was added and then brine (60 ml) the solid which precipitated of filtered off, washed with 10% brine and dried to give product (91.1% strength, 22 g).

Workup

  1. customThe reaction solvent was removed under reduced pressure, water (50 ml)
  2. additionwas added
  3. custombrine (60 ml) the solid which precipitated
  4. filtrationof filtered off
  5. washwashed with 10% brine
  6. customdried
  7. customto give product (91.1% strength, 22 g)

Sources & evidence

ORD record
ord-fe1ef58b8c64429ab6caf2f77af6a2c5
Source dataset
uspto-grants-2014_02
Patent number
US08647425B2

Linked notes

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