2-Methylpropylenediamine → 3,3-Dimethyl-1lambda~6~,2,5-thiadiazolidine-1,1-dione

HRID 1613631Notes

Reaction equation

HRID 1613631 reaction equation
[S:1]([NH2:5])([NH2:4])(=[O:3])=[O:2].N[CH2:7][C:8](N)([CH3:10])[CH3:9]>N1C=CC=CC=1>[CH3:7][C:8]1([CH3:10])[CH2:9][NH:5][S:1](=[O:3])(=[O:2])[NH:4]1

Participants

4

Reactant 2

HCID 131282-MethylpropylenediamineHCID 82267Sulfamide

Product 1

HCID 102612483,3-Dimethyl-1lambda~6~,2,5-thiadiazolidine-1,1-dioneYield 85%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a refluxing solution of sulfamide (27.25 g, 283 mmol) in anhydrous pyridine (300 ml) was added dropwise 1,2-diamino-2-methylpropane (25 g, 283 mmol) over 2 hours. The resulting mixture was refluxed for further 16 hours under nitrogen before the solvent was removed under vacuum. The residue was triturated with hexane and the solid was collected by filtration and purified by flash chromatography (silica gel, dichloromethane-methanol 96:4) to give 36.1 g (85%) of the title compound as a white solid; mp 80°-83° C.; δH (360 MHz, DMSO-d6) 7.08 (1H, br t, --NH--), 6.77 (1H, s, --NH--), 3.04 (2H, d, J=6.9 Hz, --CH2 --), 1.24 (6H, s, --CMe2); m/z (EI) 151 (M+ +1).

Workup

  1. temperatureThe resulting mixture was refluxed for further 16 hours under nitrogen before the solvent
  2. customwas removed under vacuum
  3. customThe residue was triturated with hexane
  4. filtrationthe solid was collected by filtration
  5. custompurified by flash chromatography (silica gel, dichloromethane-methanol 96:4)

Sources & evidence

ORD record
ord-a218ffadf4e0436b962d311abd337800
Source dataset
uspto-grants-1993_03
Patent number
US05194440

Reaction notes

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