Chlorosuccinimide → 1-Chloro-2-(4-methylsulfonylphenyl)-3-phenylazulene

HRID 1456826Notes

Reaction equation

HRID 1456826 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:20]=[C:19]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=[CH:18]3)[C:12]=2[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].[Cl:27]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Cl:27][C:20]1[C:19]2[C:13]([CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[C:12]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:11]=1[C:8]1[CH:7]=[CH:6][C:5]([S:2]([CH3:1])(=[O:3])=[O:4])=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 221071632-(4-Methylsulfonylphenyl)-1-phenylazulene

Product 1

HCID 221071831-Chloro-2-(4-methylsulfonylphenyl)-3-phenylazuleneYield 45.6%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 2-(4-methylsulfonylphenyl)-1-phenylazulene (0.20 g) in CCl4 (10.0 ml) was added N-chlorosuccinimide (0.08 g) and α,α'-azobis(isobuthyronitrile) (0.01 g), and the reaction mixture was heated under reflux for 1 hr. The mixture was filtered, and concentrated. The crude product was purified by SiO2 column chromatography (benzene/EtOAc, 20:1) to give the title compound (0.10 g) as green crystals; mp 140°-142° C.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureunder reflux for 1 hr
  3. filtrationThe mixture was filtered
  4. concentrationconcentrated
  5. customThe crude product was purified by SiO2 column chromatography (benzene/EtOAc, 20:1)

Sources & evidence

ORD record
ord-df876c617fd641b5b3a8184e1e14e9b5
Source dataset
uspto-grants-1998_12
Patent number
US05843999

Reaction notes

Loading…