N-Benzylethylenediamine → 2-Benzyl-1,2,5-thiadiazolidine 1,1-dioxide

HRID 1613636Notes

Reaction equation

HRID 1613636 reaction equation
[S:1](N)(N)(=[O:3])=[O:2].[CH2:6]([NH:13][CH2:14][CH2:15][NH2:16])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>N1C=CC=CC=1>[CH2:6]([N:13]1[CH2:14][CH2:15][NH:16][S:1]1(=[O:3])=[O:2])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 77801N-BenzylethylenediamineHCID 82267Sulfamide

Product 1

HCID 103758902-Benzyl-1,2,5-thiadiazolidine 1,1-dioxideYield 79%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a refluxing solution of sulfamide (27.12 g, 282 mmol) in anhydrous pyridine (250 ml) was added dropwise N-benzylethylenediamine (42.4 ml, 282 mmol) over 3 hours. The resulting solution was refluxed under nitrogen for a further 16 hours before the solvent was removed under vacuum. The residue was dissolved in dichloromethane (100 ml) and washed with 2N hydrochloric acid (1×100 ml). The aqueous layer was extracted with dichloromethane (2×100 ml) and the combined organic solutions were washed with brine (50 ml), dried (Na2SO4) and concentrated. Flash chromatography of the residue (silica gel, dichloromethane-methanol 95:5) gave 47.3 g (79%) of the title compound as a white solid; δH (360 MHz, CDCl3) 7.32 (5H, m, Ph), 4.34 (1H, br s, --NH--), 4.18 (2H, s, Ar--CH2N--), 3.47 (2H, q, J= 6.4 Hz,--CH2NH--),3.27(2H, t, J=6.4 Hz,--CH2 --); m/z (CI) 213 (M+ +1).

Workup

  1. temperatureThe resulting solution was refluxed under nitrogen for a further 16 hours before the solvent
  2. customwas removed under vacuum
  3. dissolutionThe residue was dissolved in dichloromethane (100 ml)
  4. washwashed with 2N hydrochloric acid (1×100 ml)
  5. extractionThe aqueous layer was extracted with dichloromethane (2×100 ml)
  6. washthe combined organic solutions were washed with brine (50 ml)
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-6c2d34b74ca8461799d4964f1918473f
Source dataset
uspto-grants-1993_03
Patent number
US05194440

Reaction notes

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