Hydrochloric Acid → HCID 70382339, compound

HRID 745657Notes

Reaction equation

HRID 745657 reaction equation
CC(C)([O-])C.[K+].[O:7]=[C:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[S:10](=[O:18])(=[O:17])[N:9]1[CH2:19][C:20]([O:22][CH2:23][CH2:24][OH:25])=[O:21].Cl>CS(C)=O>[OH:7][C:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[S:10](=[O:18])(=[O:17])[NH:9][C:19]=1[C:20]([O:22][CH2:23][CH2:24][OH:25])=[O:21]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 23665647Potassium tert-butoxideHCID 33665891HCID 33665891, compound

Product 1

HCID 70382339HCID 70382339, compoundYield 67.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a mixture, cooled at 18° C., of 19 g (0.17 mole) of potassium tert-butoxide in 100 ml of dimethylsulfoxide, 13.2 g (0.046 mole) of 2-hydroxyethyl 3-oxo-1,2-benzoisothiazoline-2-acetate 1,1-dioxide prepared in Example 1 are slowly added. The mixture is stirred for 10 minutes at room temperature and then rapidly dropped into 700 ml of 10% hydrochloric acid while cooling externally to 0°-5° C. The precipitate is kept under stirring at this temperature for 1-2 hours, then it is collected and washed with methylene chloride to give, after drying, 8.8 g (yield 67%) of 2-hydroxyethyl 4-hydroxy-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide, m.p. 158°-159° C., Rf 0.57 (TLC as in Example 1).

Workup

  1. additionare slowly added
  2. temperaturewhile cooling externally to 0°-5° C
  3. stirringunder stirring at this temperature for 1-2 hours
  4. customit is collected
  5. washwashed with methylene chloride
  6. customto give
  7. customafter drying

Sources & evidence

ORD record
ord-21469bdeed6f427aaa61df869578c179
Source dataset
uspto-grants-1986_07
Patent number
US04599406

Reaction notes

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