Ammonia → Hydrochloric Acid

HRID 2372646Notes

Reaction equation

HRID 2372646 reaction equation
[NH3:1].[Cl:2][S:3]([C:6]1[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[C:7]=1[C:8](OC)=[O:9])(=[O:5])=[O:4]>O1CCCC1>[ClH:2].[F:16][C:12]1[C:7]2[C:8](=[O:9])[NH:1][S:3](=[O:5])(=[O:4])[C:6]=2[CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 14257491Methyl 2-(chlorosulfonyl)-6-fluorobenzoate

Product 2

HCID 313Hydrochloric AcidHCID 142574924-Fluoro-2,3-dihydro-1lambda6,2-benzothiazole-1,1,3-trione

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

At 20° to 28° C. and while stirring, 42.5 g of ammonia was gassed into a mixture of 252.6 g (1 mol) of methyl 2-chlorosulfonyl-6-fluorobenzoate in 700 ml of anhydrous tetrahydrofuran. After the mixture had been stirred for an hour at 25° C., the precipitate was filtered off, dissolved in water, and extracted once with ethyl acetate. Acidification of the aqueous phase with concentrated hydrochloric acid gave 4% of theory of 4-fluoro-1,2-benzisothiazol-3-one-1,1-dioxide of m.p. 210° to 212° C.

Workup

  1. stirringAfter the mixture had been stirred for an hour at 25° C.
  2. filtrationthe precipitate was filtered off
  3. dissolutiondissolved in water
  4. extractionextracted once with ethyl acetate

Sources & evidence

ORD record
ord-16c167fb9268437b80a37b278d774aa7
Source dataset
uspto-grants-1992_03
Patent number
US05100459

Reaction notes

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