Azobisisobutyronitrile → HCID 69116061, compound

HRID 2054160Notes

Reaction equation

HRID 2054160 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=2)=[O:9])=[CH:4][CH:3]=1.[Br:17]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[Br:17][CH2:16][C:13]1[CH:14]=[CH:15][C:10]([S:8]([C:5]2[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][CH:6]=2)=[O:9])=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 15680p-Tolyl sulfoxideHCID 67184N-bromobutanimide

Product 1

HCID 69116061HCID 69116061, compoundYield 78.1%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 4-methyl-1-[(4-methylphenyl)sulfinyl]benzene (1.15 g, 5.00 mmol), N-bromosuccinimide (1.08 g, 6.00 mmol), 2,2′-azobis-(2-methylpropionitrile) (100 mg, 0.600 mmol), and CCl4 (25.0 mL) as solvent was stirred for 5 min at room temperature and then heated to reflux for 12 h. The reaction mixture was cooled to room temperature and filtered and the solvent was removed in vacuo, affording a crude product which was used in the next step without any further purification (1.21 g, 78.1% yield). 1H NMR (CDCl3) δ 7.71-7.57 (m, 2H), 7.57-7.40 (m, 4H), 7.36-7.16 (m, 2H), 4.46 (s, 2H), 2.37 (s, 3H).

Workup

  1. temperatureheated
  2. temperatureto reflux for 12 h
  3. temperatureThe reaction mixture was cooled to room temperature
  4. filtrationfiltered
  5. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-2f31e177570b48f193f8bcf0bc0c65ba
Source dataset
uspto-grants-2008_02
Patent number
US07329656B2

Reaction notes

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