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

HRID 1995397Notes

Reaction equation

HRID 1995397 reaction equation
C(O)C.[NH3:4].[Cl:5][C:6]1[C:11]([C:12](OC)=[O:13])=[C:10]([S:16](Cl)(=[O:18])=[O:17])[CH:9]=[CH:8][CH:7]=1>O1CCOCC1>[Cl:5][C:6]1[C:11]2[C:12](=[O:13])[NH:4][S:16](=[O:18])(=[O:17])[C:10]=2[CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 702EthanolHCID 20488465Methyl 2-chloro-6-(chlorosulfonyl)benzoate

Product 1

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

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

150 ml of ethanol saturated with ammonia were added dropwise over a period of 30 minutes to a solution of 38.2 gm (0.141 mol) of methyl 6-chloro-2-chlorosulfonyl-benzoate in 150 ml of dioxane at 30°-50° C. Subsequently, the reaction mixture was heated for 2 hours at 40° C. and for 2 hours more at 60° C. After cooling, the reaction mixture was evaporated, treated with ether and filtered. The filter cake was boiled with water, filtered while hot, and the filtrate was acidified with hydrochloric acid. Yield: 19.8 gm (64.5% of theory) of 4-chloro-1,2-benzoisothiazol-3(2H)-one-1,1-dioxide.

Workup

  1. temperatureAfter cooling
  2. customthe reaction mixture was evaporated
  3. additiontreated with ether
  4. filtrationfiltered
  5. filtrationfiltered while hot, and the filtrate

Sources & evidence

ORD record
ord-c2816ebd1cd043dab011dee6b95df96c
Source dataset
uspto-grants-1983_09
Patent number
US04404230

Reaction notes

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