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

HRID 1979981Notes

Reaction equation

HRID 1979981 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].CC(C)([O-])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 23665647Potassium tert-butoxide2×

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

To 27 ml. of dimethylsulfoxide containing 5.18 g. (26.3 mmoles) of N-methylsaccharin and 4.6 ml. (52.5 mmoles) of methyl chloroacetate at 25° C. was added 14.1 g. (126 mmoles) of potassium t-butoxide in 44 ml. of the same solvent at the rate of 0.1 ml. every minute. After 42.2 ml. of the potassium t-butoxide solution had been added the addition was stopped. During the addition the reaction temperature was maintained at about 30°-32° C.

Workup

  1. additionthe addition
  2. additionDuring the addition the reaction temperature
  3. temperaturewas maintained at about 30°-32° C.

Sources & evidence

ORD record
ord-e5e8a7fa8631404ca59fa9ec083d3e6f
Source dataset
uspto-grants-1984_11
Patent number
US04483982

Reaction notes

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