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

HRID 2291648Notes

Reaction equation

HRID 2291648 reaction equation
S(OC)(O[CH3:5])(=O)=O.[OH:8][C:9]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[S:12](=[O:20])(=[O:19])[NH:11][C:10]=1[C:21]([O:23][CH:24]([CH3:26])[CH3:25])=[O:22].[OH-].[Na+]>O.C(O)(C)C>[OH:8][C:9]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[S:12](=[O:19])(=[O:20])[N:11]([CH3:5])[C:10]=1[C:21]([O:23][CH:24]([CH3:26])[CH3:25])=[O:22]

Participants

6

Reactant 3

HCID 6497Dimethyl SulfateHCID 14798Sodium HydroxideHCID 546870271-Methylethyl 4-hydroxy-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide

Product 1

HCID 54686201Isopropyl-4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylate-1,1-dioxide

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 3776IsopropanolSolvent

Procedure

1,425 ml (15 mol) of dimethyl sulfate are added at between 10° and 15° C. to a solution of 2,833 g (10 mol) of isopropyl 4-hydroxy-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide and 440 g (11 mol) of sodium hydroxide in 4 l of water and 11.3 l of isopropanol. The mixture is maintained with stirring for 4 hours at room temperature, diluted with 28 l of water and cooled to 0°-5° C. The precipitate obtained is centrifuged, washed with cold water and dried, 2.675 g (90%) of a white or slightly pink solid, m.p. 102°-3° C. (104°-5° C. from methanol), being obtained.

Workup

  1. temperatureThe mixture is maintained
  2. temperaturecooled to 0°-5° C
  3. customThe precipitate obtained
  4. washwashed with cold water
  5. customdried
  6. custom2.675 g (90%) of a white or slightly pink solid, m.p. 102°-3° C. (104°-5° C. from methanol), being obtained

Sources & evidence

ORD record
ord-ea74256aa33d4eb9acd9b31af126c437
Source dataset
uspto-grants-1989_01
Patent number
US04797483

Reaction notes

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