Methyl iodide → 7-Bromo-2-methylsulfanyl-1,3-benzothiazole

HRID 389577Notes

Reaction equation

HRID 389577 reaction equation
C(=O)([O-])[O-].[K+].[K+].[Br:7][C:8]1[C:16]2[S:15][C:14](=[S:17])[NH:13][C:12]=2[CH:11]=[CH:10][CH:9]=1.CI.[CH3:20]COC(C)=O>CN(C=O)C>[Br:7][C:8]1[C:16]2[S:15][C:14]([S:17][CH3:20])=[N:13][C:12]=2[CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 118507717-Bromobenzo[D]thiazole-2-thiol

Product 1

HCID 667606187-Bromo-2-methylsulfanyl-1,3-benzothiazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium carbonate (67 mg, 0.49 mmol) was added to a solution of 7-bromo-1,3-benzothiazole-2(3H)-thione (100 mg, 0.41 mmol) in DMF (5 mL). The mixture was stirred at room temperature for 30 min. Methyl iodide (25 μL, 0.41 mmol) was added and the resulting mixture was stirred at room temperature for 30 min. EtOAc was added the separated organic fraction was washed with water and brine, dried over sodium sulfate, and concentrated. The title compound thus obtained was used without further purification. MS (ESI): 260.34, 262.32 [M+H]+; HPLC tR=1.54 min (HPLC: Anayltical—2 min).

Workup

  1. stirringthe resulting mixture was stirred at room temperature for 30 min
  2. washwas washed with water and brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-3c50b97598664657871d1c3bcc18f2be
Source dataset
uspto-grants-2013_02
Patent number
US08378104B2

Reaction notes

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