Benzoyl Peroxide → 2-(Bromomethyl)-7-chloro-1,3-benzothiazole

HRID 722107Notes

Reaction equation

HRID 722107 reaction equation
[Cl:1][C:2]1[C:10]2[S:9][C:8]([CH3:11])=[N:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.[Br:12]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:12][CH2:11][C:8]1[S:9][C:10]2[C:2]([Cl:1])=[CH:3][CH:4]=[CH:5][C:6]=2[N:7]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 10583610HCID 10583610, compound

Product 1

HCID 218828992-(Bromomethyl)-7-chloro-1,3-benzothiazole

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 7-chloro-2-methyl-benzothiazole (1.00 g, 5.45 mmol), N-bromosuccinimide (1.26 g, 7.08 mmol), benzoyl peroxide (0.1 g), and CCl4 (10 mL was heated to reflux under irradiation of a UV lamp for 14 h. The reaction mixture was cooled and filtered to remove the succinimide formed in the reaction, and the filtrate was evaporated to dryness. The resulting solid was purified by flash chromatography to give the title lamp (400 mg, 1.5 mmol). 1H-NMR (CDCl3): δ 7.94 (d, 1H), 7.47 (t, 1H), 7.42 (d, 1H), 4.82 (s, 2H, CH2). HPLC Rt: 7.19 min.

Workup

  1. temperaturewas heated
  2. temperatureto reflux under irradiation of a UV lamp for 14 h
  3. temperatureThe reaction mixture was cooled
  4. filtrationfiltered
  5. customto remove the succinimide
  6. customformed in the reaction
  7. customthe filtrate was evaporated to dryness
  8. customThe resulting solid was purified by flash chromatography
  9. customto give the title lamp (400 mg, 1.5 mmol)

Sources & evidence

ORD record
ord-a139d2f85fc1428581b4d72518d71dd6
Source dataset
uspto-grants-2006_11
Patent number
US07138401B2

Reaction notes

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