N-bromobutanimide → HCID 68277893, compound

HRID 409336Notes

Reaction equation

HRID 409336 reaction equation
[CH3:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([O:11][C:12]([F:15])([F:14])[F:13])[CH:8]=[CH:7][C:5]=2[N:6]=1.C1C(=O)N([Br:23])C(=O)C1>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:23][CH2:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([O:11][C:12]([F:13])([F:15])[F:14])[CH:8]=[CH:7][C:5]=2[N:6]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 23571639HCID 23571639, compound

Product 1

HCID 68277893HCID 68277893, compoundYield 38.2%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 2-methyl-6-(trifluoromethoxy)benzo[d]thiazole (9 g, 0.0386 mol) and NBS (6.9 g, 0.0386 mol) and benzoyl peroxide (0.25 g) in CCl4 (250 ml) was heated to reflux under lamp light (150 Watt) for 4 hr. Then the mixture was filtered, evaporated and purified using the Combi-Flash instrument to give 4.3 g (28.5%) of di-bromo product, 3.1 g (34%) of starting material and 4.6 g (38.2%) of 2-(bromomethyl)-6-(trifluoromethoxy)benzo[d]thiazole.

Workup

  1. temperaturewas heated
  2. temperatureto reflux under lamp light (150 Watt) for 4 hr
  3. filtrationThen the mixture was filtered
  4. customevaporated
  5. custompurified

Sources & evidence

ORD record
ord-d7b8e3f8b0964d6cb1d3c4651e7addb3
Source dataset
uspto-grants-2014_06
Patent number
US08759382B2

Reaction notes

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