N-bromobutanimide → HCID 22107203, compound

HRID 1456823Notes

Reaction equation

HRID 1456823 reaction equation
BrC1C(C2C=CC(SC)=CC=2)=C([C:12]([O:14][CH3:15])=[O:13])C2C=1C=CC=CC=2.[CH3:24][S:25]([C:28]1[CH:33]=[CH:32][C:31]([C:34]2[CH:43]=[C:42]3[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=[CH:41]3)[C:35]=2[C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)=[CH:30][CH:29]=1)(=[O:27])=[O:26].BrN1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.N(C(C)(C)C#N)=NC(C)(C)C#N>[CH3:24][S:25]([C:28]1[CH:29]=[CH:30][C:31]([C:34]2[C:35]([C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=3)=[C:36]3[C:42](=[CH:41][CH:40]=[CH:39][CH:38]=[CH:37]3)[C:43]=2[C:12]([O:14][CH3:15])=[O:13])=[CH:32][CH:33]=1)(=[O:26])=[O:27]

Participants

6

Reactant 3

HCID 67184N-bromobutanimideHCID 221071632-(4-Methylsulfonylphenyl)-1-phenylazuleneHCID 53912080Methyl 3-bromo-2-(4-methylthiophenyl)azulene-1-carboxylate

Product 1

HCID 22107203HCID 22107203, compound

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

Methyl 3 -bromo-2-(4-methylthiophenyl)azulene-1-carboxylate: To a solution of 2-(4-methylsulfonylphenyl)-1-phenylazulene (2.00 g) in CCl4 (20.0 ml) was added N-bromosuccinimide (1.26 g) and α,α'-azobis(isobutyronitrile) (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/Et2O, 100:1) to give the title compound (2.40 g) as violet crystals; mp 98°-100° 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/Et2O, 100:1)

Sources & evidence

ORD record
ord-6221883c2bad4587af956cb00bdb8a0a
Source dataset
uspto-grants-1998_12
Patent number
US05843999

Reaction notes

Loading…