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

HRID 2067323Notes

Reaction equation

HRID 2067323 reaction equation
[CH2:1]([NH:8][CH2:9][CH2:10][NH2:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[S:12](N)(N)(=[O:14])=[O:13]>N1C=CC=CC=1>[CH2:1]([N:8]1[CH2:9][CH2:10][NH:11][S:12]1(=[O:14])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 77801N-BenzylethylenediamineHCID 82267Sulfamide

Product 1

HCID 103758902-Benzyl-1,2,5-thiadiazolidine 1,1-dioxideYield 40%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of N-benzylethane-1,2-diamine (1.00 g, 6.65 mmol) in pyridine (10 mL) was added sulfamide (0.77 g, 7.98 mmol). The mixture was refluxed for 16 hours. The solvent was removed in vacuo. The residue was diluted with ethyl acetate (100 mL), washed with water (200 mL) and brine (100 mL). The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography eluted with ethyl acetate/hexane (1/4) to afford the title compound as an oily solid in 40% yield (0.57 g): 1H NMR (300 MHz, CDCl3) δ 7.35-7.27 (m, 5H), 4.59 (br s, 1H), 4.15 (s, 2H), 3.48-3.42 (m, 2H), 3.27-3.22 (m, 2H); MS (ES+) m/z 213.2 (M+1).

Workup

  1. temperatureThe mixture was refluxed for 16 hours
  2. customThe solvent was removed in vacuo
  3. additionThe residue was diluted with ethyl acetate (100 mL)
  4. washwashed with water (200 mL) and brine (100 mL)
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by column chromatography
  9. washeluted with ethyl acetate/hexane (1/4)

Sources & evidence

ORD record
ord-29b3021cc9234338995cb6d7f8568a7b
Source dataset
uspto-grants-2012_10
Patent number
US08293768B2

Reaction notes

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