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

HRID 1979982Notes

Reaction equation

HRID 1979982 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].CS(C)=O.C[O-].[Na+]>CO>[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

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 7295Methyl chloroacetateHCID 272902-methyl-1,2-benzisothiazol-3(2H)-one 1,1-dioxideHCID 10942334Sodium Methoxide2×

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of 9.86 g. (50 mmoles) of N-methylsaccharin and 10.8 ml. of methyl chloroacetate (123.8 mmoles) in 50 ml. of dimethylsulfoxide was added at the rate of 0.15 ml./minute 9.2 g. (170 mmoles) of sodium methoxide in 30 ml. of methanol. After the addition was complete an additional 2.7 g. (50 mmoles) of sodium methoxide in 11 ml. of methanol was added at the same rate for a total addition time of about 6 hours.

Workup

  1. additionAfter the addition

Sources & evidence

ORD record
ord-c84fd137d68d4e9681e8835999c5a9ad
Source dataset
uspto-grants-1984_11
Patent number
US04483982

Reaction notes

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