Methyl iodide → 3-methylthio-2H-1,4-benzothiazine

HRID 434765Notes

Reaction equation

HRID 434765 reaction equation
[H-].[Na+].[S:3]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[NH:6][C:5](=[S:13])[CH2:4]1.[CH3:14]I>CN(C)C=O>[CH3:14][S:13][C:5]1[CH2:4][S:3][C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 7739812H-1,4-Benzothiazine-3(4H)-thione

Product 1

HCID 125454293-methylthio-2H-1,4-benzothiazine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a one liter flask is placed 10.8 parts of prewashed sodium hydride in 150 parts of N,N-dimethyl-formamide (DMF) at room temperature. After stirring for five minutes under nitrogen atmosphere, 30 parts of 2H-1,4-benzothiazine-3(4H)-thione[J. Med. Chem., 12, 290(1969)] is added in portions over a period of 30 minutes and continuously stirred at room temperature for 20 minutes. To the reaction mixture is then added 15 parts of methyl iodide and the mixture stirred at room temperature for 20 minutes under nitrogen. Removal of solvent by vacuum distillation under nitrogen affords 3-methylthio-2H-1,4-benzothiazine as the residue. Since the product is subject to spontaneous hydrolytic decomposition, it is not usually isolated for the purposes of this invention but instead employed as the solution in DMF preparable via the foregoing procedure.

Workup

  1. customIn a one liter flask is placed
  2. customat room temperature
  3. stirringcontinuously stirred at room temperature for 20 minutes
  4. stirringthe mixture stirred at room temperature for 20 minutes under nitrogen
  5. customRemoval of solvent
  6. distillationby vacuum distillation under nitrogen

Sources & evidence

ORD record
ord-bdc6ff1586e144fa83a26086d1b24a7f
Source dataset
uspto-grants-1983_08
Patent number
US04399279

Reaction notes

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