Pseudosaccharin chloride → 3-[(1,1-Dioxido-1,2-benzisothiazol-3-YL)amino]-2-thioxo-1,3-thiazolidin-4-one

HRID 2172830Notes

Reaction equation

Cl[C:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[S:4](=[O:12])(=[O:11])[N:3]=1.[NH2:13][N:14]1[C:18](=[O:19])[CH2:17][S:16][C:15]1=[S:20]>O1CCOCC1>[O:19]=[C:18]1[CH2:17][S:16][C:15](=[S:20])[N:14]1[NH:13][C:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[S:4](=[O:12])(=[O:11])[N:3]=1

Participants

Conditions

Temperature: 110 °C

Procedure

To a solution of o-sulfobenzimide (5.00 g) in dioxane (20 ml) were added thionyl chloride (7.5 ml) and dimethylformamide (0.25 ml), and the mixture was stirred overnight at 110° C. The reaction mixture was concentrated under reduced pressure, and to the residue was added toluene (20 ml) to give 3-chloro-1,2-benzisothiazole 1,1-dioxide (3.77 g) as crystals. The obtained 3-chloro-1,2-benzisothiazole 1,1-dioxide (3.77 g) was dissolved in dioxane (20 ml), 3-aminorhodanine (2.77 g) was added thereto, and the mixture was stirred at 110° C. for 1 hr. The reaction mixture was concentrated under reduced pressure, and to the residue was added chloroform (20 ml) to give 3-[(4-oxo-2-thioxothiazolidin-3-yl)amino]-1,2-benzisothiazole 1,1-dioxide (3.56 g).

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
additionto the residue was added chloroform (20 ml)

Sources & evidence

ORD record: ord-a0e0025a28a142179f6c5a4e43c3521e
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09056862B2

Reaction notes

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