2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 10060389, compound

HRID 1956961Notes

Reaction equation

HRID 1956961 reaction equation
[CH3:1][O:2][C:3]1[C:4]([CH:16]([CH3:18])[CH3:17])=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[CH:9]=[CH:8][CH:7]([CH3:15])[CH2:6]2.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>C1C=CC=CC=1>[CH3:14][O:13][C:12]1[C:3]([O:2][CH3:1])=[C:4]([CH:16]([CH3:17])[CH3:18])[C:5]2[C:10](=[CH:9][CH:8]=[C:7]([CH3:15])[CH:6]=2)[CH:11]=1

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 10014812HCID 10014812, compound

Product 1

HCID 10060389HCID 10060389, compoundYield 95.1%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Compound 12 (3.00 g, 12.2 mmol) was dissolved in 25 mL of benzene and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (2.80 g, 12.2 mmol) was added slowly with stirring and stirring was continued for 3 h. The reaction mixture was filtered through a short column of alumina which was washed with dichloromethane. The solvent was evaporated from the colorless eluant and the residual product was crystallized from petroleum ether to give 2.83 g (11.6 mmol, 95%) of 18 as colorless microcrystalline plates: mp 62°-63° C.; 1H NMR: δ 1.51 (d, J=7.2 Hz, 6 H), 2.50 (s, 3 H), 3.88 (s, 3 H), 3.90 (sept, J=7.2 Hz, 1 H), 3.94 (s, 3 H), 7.01 (s, 1 H), 7.20 (d, J=8.3 Hz, 1 H), 7.60 (d, J=8.3 Hz, 1 H), 7.88 (s, 1 H). Anal. (C16H20O2) C, H.

Workup

  1. stirringstirring
  2. filtrationThe reaction mixture was filtered through a short column of alumina which
  3. washwas washed with dichloromethane
  4. customThe solvent was evaporated from the colorless eluant
  5. customthe residual product was crystallized from petroleum ether

Sources & evidence

ORD record
ord-dc3f273a565640cdba2c8f66edfd2265
Source dataset
uspto-grants-1998_07
Patent number
US05780675

Reaction notes

Loading…