Pseudosaccharin chloride → HCID 178483221, compound

HRID 1154715Notes

Reaction equation

HRID 1154715 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[O:9][C:8]([CH2:10][S:11][CH2:12][CH2:13][NH2:14])=[CH:7][CH:6]=1)[CH3:3].Cl[C:16]1[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[S:18](=[O:26])(=[O:25])[N:17]=1>C(Cl)(Cl)Cl>[CH3:3][N:2]([CH2:4][C:5]1[O:9][C:8]([CH2:10][S:11][CH2:12][CH2:13][NH:14][C:16]2[C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=3[S:18](=[O:25])(=[O:26])[N:17]=2)=[CH:7][CH:6]=1)[CH3:1]

Participants

4

Reactant 2

HCID 64783Pseudosaccharin chlorideHCID 1622035-(((2-Aminoethyl)thio)methyl)-N,N-dimethyl-2-furanmethanamine

Product 1

HCID 178483221HCID 178483221, compoundYield 12%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a refluxing solution of 2.14 g (10 mmol) of 2-[[[5-[(dimethylamino)methyl]-2-furanyl]methyl]thio]ethylamine in 150 ml of chloroform is added incrementally 2.02 g (10 mmol) of 3-chlorobenzisothiazole 1,1-dioxide. The reaction mixture is refluxed for an additional 30 minutes, is cooled to room temperature and then solvent is removed on a rotoevaporator. The resulting oil is subjected to preparative column chromatography on silica gel. Elution with methylene chloride followed by methylene chloride: methanol (95:5) yields 420 mg (12%) of a white solid. The solid is suspended in ethyl ether, separated by suction filtration and dried in vacuo to give 270 mg (7%) of the title compound: m.p. 91-94.C.

Workup

  1. temperatureThe reaction mixture is refluxed for an additional 30 minutes
  2. customsolvent is removed on a rotoevaporator
  3. washElution with methylene chloride

Sources & evidence

ORD record
ord-2c19b701247346c4be112aa8c5e4bbc9
Source dataset
uspto-grants-1984_12
Patent number
US04490527

Reaction notes

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