N-bromobutanimide → HCID 18941095, compound

HRID 865107Notes

Reaction equation

HRID 865107 reaction equation
[CH3:1][C:2]1[S:3][C:4]2[CH:14]=[CH:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:5]=2[N:6]=1.[Br:15]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:15][CH2:1][C:2]1[S:3][C:4]2[CH:14]=[CH:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:5]=2[N:6]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 75892Naphtho[1,2-d]thiazole, 2-methyl-

Product 1

HCID 18941095HCID 18941095, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

To 3.98 g of 2-methylnaphtho[1,2-d]thiazole dissolved in carbon tetrachloride (40 ml) was added 3.56 g of N-bromosuccinimide and 0.20 g of benzoyl peroxide, followed by 6 hours of heating under reflux. After cooling the reaction solution, insoluble matter was removed by filtration, and the solvent was evaporated. The residue was subjected to silica gel column chromatography eluted with hexane-chloroform (5:1) to obtain 3.50 g (63%) of 2-bromomethylnaphtho[1,2-d]thiazole.

Workup

  1. temperatureof heating
  2. temperatureunder reflux
  3. temperatureAfter cooling the reaction solution, insoluble matter
  4. customwas removed by filtration
  5. customthe solvent was evaporated
  6. washeluted with hexane-chloroform (5:1)

Sources & evidence

ORD record
ord-13d380465b7a413fade7138bad7130a2
Source dataset
uspto-grants-1996_10
Patent number
US05565479

Reaction notes

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