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

HRID 1776231Notes

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

Conditions

Temperature: 120 °C

Procedure

To a stirred mixture of N-benzylethylenediamine (2.000 g, 13.3 mmol) in pyridine (20 mL) was added sulfamide (1.919 g, 20.0 mmol). The mixture was heated in an oil bath at 120° C. for 16 hrs. After cooling to room temperature, the mixture was concentrated and the residue was partitioned between ethyl acetate and saturated aqueous sodium chloride. The organic layer was washed with 1 N aqueous hydrochloric acid, saturated aqueous sodium chloride, dried (anhydrous sodium sulfate), filtered, and concentrated. The residue was purified by silica gel chromatography (0-80% ethyl acetate/hexanes) to afford the product as a light yellow thick oil (1.4 g, 50%). 1H NMR (300 MHz, CDCl3) δ 7.40-7.30 (m, 5H), 4.38 (br s, 1H), 4.20 (s, 2H), 3.50 (q, 2H, J=6.6 Hz), 3.29 (t, 2H, J=6.6 Hz).

Workup

temperatureAfter cooling to room temperature
concentrationthe mixture was concentrated
customthe residue was partitioned between ethyl acetate and saturated aqueous sodium chloride
washThe organic layer was washed with 1 N aqueous hydrochloric acid, saturated aqueous sodium chloride
dry with materialdried (anhydrous sodium sulfate)
filtrationfiltered
concentrationconcentrated
customThe residue was purified by silica gel chromatography (0-80% ethyl acetate/hexanes)

Sources & evidence

ORD record: ord-e2d3afd3947d4943895c31d1208ff0f8
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09265772B2

Reaction notes

Loading…