Hydrochloric Acid → methyl 4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide

HRID 354639

Reaction equation

HRID 354639 reaction equation
[H-].[Na+].[CH3:3][N:4]1[C:14](=[O:15])[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[S:5]1(=[O:7])=[O:6].[CH3:16][O:17][C:18](=[O:21])[CH2:19]Cl.Cl>CS(C)=O>[OH:15][C:14]1[C:13]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[S:5](=[O:7])(=[O:6])[N:4]([CH3:3])[C:19]=1[C:18]([O:17][CH3:16])=[O:21]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7295Methyl chloroacetateHCID 24758Sodium hydrideHCID 272902-methyl-1,2-benzisothiazol-3(2H)-one 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 679Dimethyl SulfoxideSolvent

Procedure

In a manner similar to Example 6, 864 mg. (0.036 mole) of 99% sodium hydride was added over a two hour period to a solution of 2.9 g. (0.015 mole) of N-methylsaccharin and 9.8 g. (0.09 mole) of methylchloroacetate in 10 ml. of dimethylsulfoxide at 40° C. Stirring was continued at 40°-45° C. for an additional two hours, and the reaction mixture was poured into 150 ml. of 5% hydrochloric acid solution. The precipitate was filtered and dried to give 3.07 (76%) of the desired product.

Workup

  1. customat 40° C
  2. additionthe reaction mixture was poured into 150 ml
  3. filtrationThe precipitate was filtered
  4. customdried

Sources & evidence

ORD record
ord-9865dd9ec9a04768ba0cef810bfeaf60
Source dataset
uspto-grants-1983_03
Patent number
US04376204

Linked notes

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