Dimethyl Sulfate → methyl 4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide

HRID 1657399Notes

Reaction equation

HRID 1657399 reaction equation
[OH:1][C:2]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[S:5](=[O:13])(=[O:12])[NH:4][C:3]=1[C:14]([O:16][CH3:17])=[O:15].[OH-].[Na+].S(OC)(O[CH3:24])(=O)=O>O>[OH:1][C:2]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[S:5](=[O:12])(=[O:13])[N:4]([CH3:24])[C:3]=1[C:14]([O:16][CH3:17])=[O:15]

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 14798Sodium HydroxideHCID 54676531methyl 4-hydroxy-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide

Product 1

HCID 54676532methyl 4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

To a suspension of 90 grams (0.352 moles) of methyl 4-hydroxy-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide in 450 ml proprietory alcohol there is added a solution of 15.5 grams (0.3875 moles) of sodium hydroxide in 450 ml of water at a temperature of less than 20°C. 53.4 Grams (0.423 moles) of dimethyl sulphate is added while stirring, at 25°C. and the mixture is then allowed to stir for about 15 hours. It is cooled to 10°C. and filtered. The cake is washed with water, followed by a 50% alcohol/water wash, and dried. Yield is 90 grams (95%) m.p. 162.5°-164°C.

Workup

  1. stirringto stir for about 15 hours
  2. temperatureIt is cooled to 10°C.
  3. filtrationfiltered
  4. washThe cake is washed with water
  5. washwash
  6. customdried

Sources & evidence

ORD record
ord-72704eab76c740aab49d9409c73eddc4
Source dataset
uspto-grants-1976_06
Patent number
US03960856

Reaction notes

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