Methyl iodide → HCID 59277705, compound

HRID 1097774Notes

Reaction equation

HRID 1097774 reaction equation
I[CH3:2].[O:3]=[S:4]1(=[O:16])[CH2:9][C:8](=O)[C:7]2[CH:11]=[CH:12][CH:13]=[CH:14][C:6]=2[N:5]1[CH3:15].[C:17]([O-:20])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:15][N:5]1[C:6]2[CH:7]=[CH:11][CH:12]=[CH:13][C:14]=2[C:17](=[O:20])[C:9]([CH3:8])([CH3:2])[S:4]1(=[O:3])=[O:16]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 27375131-Methyl-2lambda~6~,1-benzothiazine-2,2,4(1H,3H)-trione

Product 1

HCID 59277705HCID 59277705, compoundYield 79.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

Iodomethane (187 ul, 426 mg, 3 mmol) is added dropwise to a suspension of 2,2-Dioxo-1-methyl-2,1-benzothiazin-4(3H)-one ([CAS: 7117-31-9], 220 mg, 1 mmol), K2CO3 (1.38 g, 10 mmol) in 3 mL of dry DMF at room temperature. The resulting mixture is stirred at 60° C. After 2 h, the reaction mixture is filtered, and washed with ethyl acetate (20 mL). The combined solution is concentrated and the residue is purified by flash column (ethyl acetate-heptane v/v 10%) and gives the title compound as white solid (190 mg).

Workup

  1. filtrationthe reaction mixture is filtered
  2. washwashed with ethyl acetate (20 mL)
  3. concentrationThe combined solution is concentrated
  4. customthe residue is purified by flash column (ethyl acetate-heptane v/v 10%)

Sources & evidence

ORD record
ord-43d21b9309a547dc84ed1ec1af739cd5
Source dataset
uspto-grants-2012_03
Patent number
US08143278B2

Reaction notes

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