Carbon Tetrachloride → 6-Bromomethyl-2-cyclohexyl-benzothiazole

HRID 2041215Notes

Reaction equation

HRID 2041215 reaction equation
[CH2:1]([C:8]1[S:9][C:10]2[CH:16]=[C:15]([CH3:17])[CH:14]=[CH:13][C:11]=2[N:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4]C=1.C1C(=O)N([Br:25])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C.C(Cl)(Cl)(Cl)Cl>C(Cl)(Cl)Cl>[Br:25][CH2:17][C:15]1[CH:14]=[CH:13][C:11]2[N:12]=[C:8]([CH:1]3[CH2:2][CH2:7][CH2:6][CH2:5][CH2:4]3)[S:9][C:10]=2[CH:16]=1

Participants

6

Reactant 4

HCID 5943Carbon TetrachlorideHCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 508498892-Benzyl-6-methyl-benzothiazole

Product 1

HCID 576564066-Bromomethyl-2-cyclohexyl-benzothiazoleYield 53.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Combine 2-benzyl-6-methyl-benzothiazole (0.6 g, 2.42 mmol), NBS (0.5 g, 2.54 mmol), AIBN (40 mg, 0.24 mmol), carbon tetrachloride (10 mL) and reflux for 3 h. Cool the reaction mixture to ambient temperature, dilute with chloroform and wash with water. Dry the organic extracts over anhydrous Na2SO4, concentrate in vacuo and purify by chromatography on silica gel eluting with hexane/EtOAc (1:0 and 9:1) to obtain the title compound as a white solid (0.4 g, 53%). MS (ES+) m/z: 311 (M+H)+.

Workup

  1. washwash with water
  2. dry with materialDry the organic extracts over anhydrous Na2SO4
  3. concentrationconcentrate in vacuo
  4. custompurify by chromatography on silica gel eluting with hexane/EtOAc (1:0 and 9:1)

Sources & evidence

ORD record
ord-420978880e4743449e3b52cfe2924bcd
Source dataset
uspto-grants-2013_11
Patent number
US08580780B2

Reaction notes

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