Ethyl chloroformate → HCID 22419897, compound

HRID 1720032Notes

Reaction equation

HRID 1720032 reaction equation
[F:1][C:2]1[CH:12]=[CH:11][C:5]2[CH2:6][S:7](=[O:10])(=[O:9])[NH:8][C:4]=2[CH:3]=1.Cl[C:14]([O:16][CH2:17][CH3:18])=[O:15]>N1C=CC=CC=1>[CH2:17]([O:16][C:14]([N:8]1[C:4]2[CH:3]=[C:2]([F:1])[CH:12]=[CH:11][C:5]=2[CH2:6][S:7]1(=[O:10])=[O:9])=[O:15])[CH3:18]

Participants

4

Reactant 2

HCID 10928Ethyl chloroformateHCID 22419891HCID 22419891, compound

Product 1

HCID 22419897HCID 22419897, compoundYield 87.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirred solution of 1,3-dihydro-6-fluoro-2,1-benzisothiazole-2,2-dioxide (2.57 g) in anhydrous pyridine (8 ml) was added ethyl chloroformate (1.79 g) at 0° C. under N2 atmosphere. The mixture was stirred for 30 minutes and concentrated in vacuo. Cold hydrochloric acid was added to the precipitate (pH=6). The resulting solution was extracted with ethyl acetate. The organic layer was washed with water and dried over magnesium sulfate. The crude product was purified by silica gel column chromatography (methylene chloride-ethyl acetate 95:5) to give 1-ethoxycarbonyl-1,3-dihydro-6-fluoro-2,1-benzisothiazole 2,2-dioxide (3.1 g).

Workup

  1. concentrationconcentrated in vacuo
  2. additionCold hydrochloric acid was added to the precipitate (pH=6)
  3. extractionThe resulting solution was extracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialdried over magnesium sulfate
  6. customThe crude product was purified by silica gel column chromatography (methylene chloride-ethyl acetate 95:5)

Sources & evidence

ORD record
ord-2e5ae54318224027b47ac6bfe97c1c87
Source dataset
uspto-grants-1996_04
Patent number
US05504095

Reaction notes

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