Chlorosuccinimide → HCID 58288241, compound

HRID 1476091Notes

Reaction equation

HRID 1476091 reaction equation
[Cl:1]N1C(=O)CCC1=O.[Br:9][C:10]1[C:11]([CH3:17])=[C:12]([CH:14]=[CH:15][CH:16]=1)[NH2:13]>C(#N)C>[Br:9][C:10]1[C:11]([CH3:17])=[C:12]([C:14]([Cl:1])=[CH:15][CH:16]=1)[NH2:13]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 1235383-Bromo-o-toluidine

Product 1

HCID 58288241HCID 58288241, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

At RT, 8.61 g (64.5 mmol) of N-chlorosuccinimide were added to a solution of 12.0 g (64.5 mmol) of 3-bromo-2-methylaniline in 150 ml of acetonitrile. The reaction mixture was stirred at 60° C. for 7 h and, after cooling, concentrated under reduced pressure. The residue was taken up in dichloromethane, and the mixture was washed successively with sat. sodium bicarbonate solution and sat. sodium chloride solution, dried over sodium sulphate and concentrated under reduced pressure. The crude product gave, after chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 40:1 to 20:1), 3.78 g of the target product (26.6% of theory).

Workup

  1. temperatureafter cooling
  2. concentrationconcentrated under reduced pressure
  3. washthe mixture was washed successively with sat. sodium bicarbonate solution and sat. sodium chloride solution
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-127ca8c3df3a4626baeffe540ab7138e
Source dataset
uspto-grants-2015_04
Patent number
US09018414B2

Reaction notes

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