Hydrochloric Acid → 4-fluoro-2-cyclopropylmethyl-1,2-benzisothiazol-3(2H)-imine 1,1-dioxide

HRID 470595Notes

Reaction equation

HRID 470595 reaction equation
[C:1]([C:3]1[C:8]([F:9])=[CH:7][CH:6]=[CH:5][C:4]=1[S:10](Cl)(=[O:12])=[O:11])#[N:2].[CH:14]1([CH2:17][NH2:18])[CH2:16][CH2:15]1.O.Cl>C1COCC1>[F:9][C:8]1[C:3]2[C:1](=[NH:2])[N:18]([CH2:17][CH:14]3[CH2:16][CH2:15]3)[S:10](=[O:11])(=[O:12])[C:4]=2[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 75646CyclopropanemethanamineHCID 205052122-Cyano-3-fluorobenzene-1-sulfonyl chloride

Product 1

HCID 674148304-fluoro-2-cyclopropylmethyl-1,2-benzisothiazol-3(2H)-imine 1,1-dioxide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

100 mg of 2-cyano-3-fluoro-benzenesulfonyl chloride (EP33984 A1 19810819) is added to a solution of 0.85 ml of cyclopropylmethylamin in 3.5 ml of THF. After stirring for 3 hours at room temperature the reaction mixture is poured into water. The mixture is acidified with hydrochloric acid (˜pH3) and extracted three times with methylenchloride. The combined organic phases are dried (Na2SO4), filtered and concentrated. Preparative HPLC affords 16 mg of 4-fluoro-2-cyclopropylmethyl-1,2-benzisothiazol-3(2H)-imine 1,1-dioxide as an orange solid (m.p. 90-93° C.).

Workup

  1. extractionextracted three times with methylenchloride
  2. dry with materialThe combined organic phases are dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-91856d5efe8742f6a0eaefc88d6b8d33
Source dataset
uspto-grants-2014_01
Patent number
US08629284B2

Reaction notes

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