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

HRID 1979984Notes

Reaction equation

HRID 1979984 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].C[Si](C)(C)N[Si](C)(C)C.[K]>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 45051783Silanamine, 1,1,1-trimethyl-N-(trimethylsilyl)-, potassium salt

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

To 870 mg. (4.4 mmoles) of N-methylsaccharin and 0.95 ml. (10.89 mmoles) of methyl chloroacetate in 3 ml. of dimethylsulfoxide under nitrogen was added at the rate of 0.084 ml./minute 3.99 g. (20 mmoles) of potassium hexamethyl disilazane in 9.98 ml. of dimethylsulfoxide.

Sources & evidence

ORD record
ord-5debe166629a4fe69efd29c56af595dc
Source dataset
uspto-grants-1984_11
Patent number
US04483982

Reaction notes

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