N-bromobutanimide → HCID 22107181, compound

HRID 1456830Notes

Reaction equation

HRID 1456830 reaction equation
C([NH:5][S:6]([C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:24]=[C:23]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=[CH:22]3)[C:16]=2[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:11][CH:10]=1)(=[O:8])=[O:7])(C)(C)C.BrN1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.N(C(C)(C)C#N)=NC(C)(C)C#N>[C:25]1([C:16]2[C:17]3[C:23]([CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:24][C:15]=2[C:12]2[CH:13]=[CH:14][C:9]([S:6]([NH2:5])(=[O:7])=[O:8])=[CH:10][CH:11]=2)[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 109606712-(4-t-Butylaminosulfonylphenyl)-1-phenylazulene

Product 1

HCID 22107181HCID 22107181, compoundYield 129.5%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

Methyl 3-bromo-2-(4-t-butylaminosulfonylphenyl) azulene-1-carboxylate: To a solution of 2-(4-t - butylaminosulfonylphenyl) -1-phenylazulene (0.50 g) in CCl4 (20.0 ml) was added N-bromosuccinimide (0.25 g) and α,α'-azobis (isobutyronitrile) (0.01 g), and the reaction mixture was heated under reflux for 1 hr. The reaction mixture was filtered, and concentrated. The crude product was purified by SiO2 column chromatography (benzene/EtOAc, 20:1) to give the title compound (0.56 g) as violet crystals; mp 171°-172° C.

Workup

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

Sources & evidence

ORD record
ord-8913776e13214159a611bdd40a4e6357
Source dataset
uspto-grants-1998_12
Patent number
US05843999

Reaction notes

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