N-bromobutanimide → HCID 22144497, compound

HRID 1824796Notes

Reaction equation

HRID 1824796 reaction equation
[CH3:1][C:2]1[C:7]2[N:8]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=3)[S:10][C:6]=2[CH:5]=[C:4]([O:19][CH3:20])[CH:3]=1.[Br:21]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:21][CH2:1][C:2]1[C:7]2[N:8]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=3)[S:10][C:6]=2[CH:5]=[C:4]([O:19][CH3:20])[CH:3]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 22144548HCID 22144548, compound

Product 1

HCID 22144497HCID 22144497, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

4-Methyl-6-methoxy-2-(4-methoxy-phenyl)-benzothiazole (0.53 g, 1.87 mmol), N-bromosuccinimide (0.33 g, 1.87 mmol) and benzoyl peroxide (9 mg) were suspended in carbon tetrachloride (6 mL) and refluxed for 3.5 h, then cooled to room temperature. Solvent was evaporated and the mixture was purified by chromatography to give 4-bromomethyl-6-methoxy-2-(4-methoxy-phenyl)-benzothiazole (0.47 g, 70% yield) as a white solid. Mass spec: MH+=364.

Workup

  1. temperaturerefluxed for 3.5 h
  2. customSolvent was evaporated
  3. customthe mixture was purified by chromatography

Sources & evidence

ORD record
ord-af2ea679d83d446a9311f8f3f715382b
Source dataset
uspto-grants-2006_05
Patent number
US07045539B2

Reaction notes

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