Potassium Carbonate → 4-(2-Oxiranylmethoxy)phthalonitrile

HRID 1596448Notes

Reaction equation

HRID 1596448 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:10]#[N:11])[C:5](=[CH:8][CH:9]=1)[C:6]#[N:7].C([O-])([O-])=O.[K+].[K+].[N+](C1C=C(S(O[CH2:31][CH:32]2[CH2:34][O:33]2)(=O)=O)C=CC=1)([O-])=O>CC#N>[O:33]1[CH2:34][CH:32]1[CH2:31][O:1][C:2]1[CH:3]=[C:4]([C:10]#[N:11])[C:5](=[CH:8][CH:9]=1)[C:6]#[N:7]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 286836(Oxiran-2-yl)methyl 3-nitrobenzene-1-sulfonateHCID 38757654-Hydroxybenzene-1,2-dicarbonitrile

Product 1

HCID 217019504-(2-Oxiranylmethoxy)phthalonitrile

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A stirred suspension of 4-hydroxyphthalonitrile (3.5 g; 24.3 mmol), K2CO3 (4.03 g; 29.2 mmol) and 2-{[(3-nitrophenyl)sulfonyloxy]methyl}-oxirane (6.50 g; 25.0 mmol; see Example B above) in MeCN (170 mL) was refluxed for 1.5 h. The cooled reaction mixture was filtered, the filtrate concentrated and the solid residue recrystallized from IPA to give the sub-title compound.

Workup

  1. temperaturewas refluxed for 1.5 h
  2. customThe cooled reaction mixture
  3. filtrationwas filtered
  4. concentrationthe filtrate concentrated
  5. customthe solid residue recrystallized from IPA

Sources & evidence

ORD record
ord-bd65396e053b4c58bbe1c2cd5fe5b378
Source dataset
uspto-grants-2001_09
Patent number
US06291475B1

Reaction notes

Loading…