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

HRID 1979983Notes

Reaction equation

HRID 1979983 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].Cl[CH2:15][C:16]([O:18][CH3:19])=[O:17].[O-]CC.[Na+]>CS(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:15]=1[C:16]([O:18][CH3:19])=[O:17]

Participants

5

Reactant 3

HCID 7295Methyl chloroacetateHCID 272902-methyl-1,2-benzisothiazol-3(2H)-one 1,1-dioxideHCID 2723922Sodium ethoxide

Product 1

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

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

In a manner similar to Examples 15 and 16, to a solution of 2.86 g. (50 mmoles) of N-methylsaccharin and 10.8 ml. (100 mmoles) of methyl chloroacetate in 17 ml. of dimethylsulfoxide was added 11.56 g. (170 mmoles) of sodium ethoxide in 63 ml. of dimethylsulfoxide over a period of 2.5 hours.

Sources & evidence

ORD record
ord-f6fd8fba62024f60949a4e58cac83bbe
Source dataset
uspto-grants-1984_11
Patent number
US04483982

Reaction notes

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