Methyl iodide → 2-(Methylthio)benzo[d]thiazole-5-carbonitrile

HRID 1944685Notes

Reaction equation

HRID 1944685 reaction equation
[S:1]=[C:2]1[NH:6][C:5]2[CH:7]=[C:8]([C:11]#[N:12])[CH:9]=[CH:10][C:4]=2[S:3]1.[CH3:13]CN(CC)CC.CI>CCO>[CH3:13][S:1][C:2]1[S:3][C:4]2[CH:10]=[CH:9][C:8]([C:11]#[N:12])=[CH:7][C:5]=2[N:6]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 8471TriethylamineHCID 221487542-Sulfanyl-1,3-benzothiazole-5-carbonitrile

Product 1

HCID 219858242-(Methylthio)benzo[d]thiazole-5-carbonitrileYield 97.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-thioxo-2,3-dihydrobenzothiazole-5-carbonitrile (260 mg, 1.35 mmol) in EtOH (10.8 mL) was added Et3N (137 mg, 1.35 mmol) and methyliodide (192 mg, 1.35 mmol). The mixture was heated at reflux for 1 h. The volatiles were evaporated and the residue was extracted with CH2Cl2 (3×10 mL). The combined organic extracts were washed with brine, dried (Na2SO4) and concentrated to give 2-methylsulfanylbenzothiazole-5-carbonitrile 271 mg (97%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 1 h
  3. customThe volatiles were evaporated
  4. extractionthe residue was extracted with CH2Cl2 (3×10 mL)
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-87891bb7e6484b93ad86a880886d7993
Source dataset
uspto-grants-2013_03
Patent number
US08394842B2

Reaction notes

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