Methyl chloroacetate → methyl 4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide

HRID 354638

Reaction equation

HRID 354638 reaction equation
[CH3:1][N:2]1[C:12](=[O:13])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[S:3]1(=[O:5])=[O:4].[CH3:14][O:15][C:16](=[O:19])[CH2:17]Cl.[H-].[Na+]>CN(C)C=O>[OH:13][C:12]1[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[S:3](=[O:5])(=[O:4])[N:2]([CH3:1])[C:17]=1[C:16]([O:15][CH3:14])=[O:19]

Participants

5

Reactant 3

HCID 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 6228DimethylformamideSolvent

Procedure

To a solution of 2.9 g. (0.015 mole) of N-methylsaccharin and 2.63 g. (0.03 mole) of methylchloroacetate in 10 ml. of dimethylformamide at 40° C. was added over a period of two hours 864 mg. (0.036 mole) of 99% sodium hydride. Stirring was continued for two hours, maintaining a reaction temperature of 40°-50° C. The reaction mixture was quenched in 150 ml. of 5% hydrochloric acid, and the precipitated product filtered and dried, 3.41 g. (84%).

Workup

  1. temperaturemaintaining a reaction temperature of 40°-50° C
  2. customThe reaction mixture was quenched in 150 ml
  3. filtrationof 5% hydrochloric acid, and the precipitated product filtered
  4. customdried

Sources & evidence

ORD record
ord-b8e61da925d74b23b717569ebd7c037e
Source dataset
uspto-grants-1983_03
Patent number
US04376204

Linked notes

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