Methyl iodide → HCID 20220115, compound

HRID 235646Notes

Reaction equation

HRID 235646 reaction equation
[OH:1][CH2:2][CH2:3][CH:4]1[C:9](=[O:10])[NH:8][C:7]2[CH:11]=[CH:12][CH:13]=[CH:14][C:6]=2[S:5]1.[H-].[Na+].[CH3:17]I>CN(C)C=O>[OH:1][CH2:2][CH2:3][CH:4]1[C:9](=[O:10])[N:8]([CH3:17])[C:7]2[CH:11]=[CH:12][CH:13]=[CH:14][C:6]=2[S:5]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 146849742-(2-Hydroxyethyl)-2H-1,4-benzothiazin-3(4H)-one

Product 1

HCID 20220115HCID 20220115, compoundYield 87.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4.18 g of 2-(2-hydroxyethyl)-2H-1,4-benzothiazin-3(4H)-one in 50 ml of dimethylformamide, was added portionwise 0.8 g of 60% sodium hydride in oil with stirring under ice-cooling. After the mixture was stirred for 10 minutes, 1.24 ml of methyl iodide was added thereto. The temperature of the reaction system was then reverted to room temperature and the mixture was stirred for one hour. After dilution with water, the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4) and concentrated under reduced pressure. The residue was subjected to a column chromatography on silica-gel (50 g). From the eluate with hexane-using silica-gel (50 g). From the eluate with hexane-ethyl acetate (2:1, v/v) was obtained 3.90 g (87.4%) of 2-(2-hydroxyethyl)-4-methyl-2H-1,4-benzothiazin-3(4H)-one as an oily substance.

Workup

  1. temperaturecooling
  2. stirringAfter the mixture was stirred for 10 minutes
  3. customwas then reverted to room temperature
  4. stirringthe mixture was stirred for one hour
  5. extractionAfter dilution with water, the mixture was extracted with ethyl acetate
  6. washThe ethyl acetate layer was washed with water
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-308657bb29b9485cb92375633b8f9e36
Source dataset
uspto-grants-1987_02
Patent number
US04640916

Reaction notes

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