Sodium Hydroxide → 4-Chloro-2,3-dihydro-1lambda6,2-benzothiazole-1,1,3-trione

HRID 2372644Notes

Reaction equation

HRID 2372644 reaction equation
[Cl:1][C:2]1[C:7]([C:8](OC)=[O:9])=[C:6]([S:12]([NH2:15])(=[O:14])=[O:13])[CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>O>[Cl:1][C:2]1[C:7]2[C:8](=[O:9])[NH:15][S:12](=[O:14])(=[O:13])[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 14257494HCID 14257494, compound

Product 1

HCID 155671714-Chloro-2,3-dihydro-1lambda6,2-benzothiazole-1,1,3-trione

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

504 g (2.02 mol) of methyl 6-chloro-2-aminosulfonylbenzoate was added in portions to a solution of 80 g (2.0 mol) of sodium hydroxide in 2.5 liters of water; the temperature rose from 25° C. to 50° C. After 30 minutes at this temperature, the mixture was cooled to 25° C. and extracted with methyl tert-butyl ether, and the aqueous phase was stirred into 2N hydrochloric acid. The precipitate was isolated, washed with water and dried. There was obtained 330 g (75.8% of theory) of the title compound, m.p.: 210°-212° C.

Workup

  1. customrose from 25° C. to 50° C
  2. extractionextracted with methyl tert-butyl ether
  3. customThe precipitate was isolated
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-08c0c9e1d5cb4dd19f8016662c19b93d
Source dataset
uspto-grants-1992_03
Patent number
US05100459

Reaction notes

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