N-bromobutanimide → HCID 13712239, compound

HRID 364883Notes

Reaction equation

HRID 364883 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][C:10]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][C:11]=3[N:12]=2)=[CH:4][CH:3]=1.[Br:18]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:18][CH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[S:9][C:10]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][C:11]=3[N:12]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 13712241HCID 13712241, compound

Product 1

HCID 13712239HCID 13712239, compoundYield 74.1%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

31.6 g of 2-(4-methylphenyl)-5-fluorobenzothiazole was dissolved in 660 ml of carbon tetrachloride, and 23.1 g of N-bromosuccinimide and 700 mg of benzoyl peroxide were added. The mixture was refluxed for 6 hours. The reaction mixture was cooled to room temperature, and the insoluble materials were separated by filtration. The filtrate was concentrated to a volume of 100 ml under reduced pressure. The precipitated crystals were collected by filtration to give 31.0 g of the captioned compound as crude crystals. Recrystallization from carbon tetrachloride gave the captioned compound as colorless platelike crystals.

Workup

  1. temperatureThe mixture was refluxed for 6 hours
  2. customthe insoluble materials were separated by filtration
  3. concentrationThe filtrate was concentrated to a volume of 100 ml under reduced pressure
  4. filtrationThe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-3a11598ec2244e69b1e797c6693655af
Source dataset
uspto-grants-1986_08
Patent number
US04607031

Reaction notes

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