1,2-Ethanedithiol → 1,4-Dithia-7-aza-spiro[4.4]nonane-6,8-dione

HRID 929390Notes

Reaction equation

HRID 929390 reaction equation
Br[C:2]1[C:3]([NH:5][C:6](=[O:8])[CH:7]=1)=[O:4].C([O-])(=O)C.[Na+].[CH2:14]([SH:17])[CH2:15][SH:16]>CO>[S:16]1[C:2]2([CH2:7][C:6](=[O:8])[NH:5][C:3]2=[O:4])[S:17][CH2:14][CH2:15]1

Participants

5

Reactant 3

HCID 109021,2-EthanedithiolHCID 517045Sodium AcetateHCID 118195503-bromo-2,5-dihydro-1H-pyrrole-2,5-dione

Product 1

HCID 145676511,4-Dithia-7-aza-spiro[4.4]nonane-6,8-dioneYield 41.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To bromomaleimide (30 mg, 0.17 mmol) and sodium acetate (14 mg, 0.17 mmol) in methanol (6 mL) was added 1,2-ethanedithiol (17 μl 0.17 mmol). After five minutes solvent removed in vacuo and purification by flash chromatography (10% ethyl acetate in petroleum ether) afforded the desired compound as a pale yellow powder (13 mg, 0.07 mmol) in 41% yield. δH (500 MHz, CDCl3) 8.39 (s, 1H, NH), 3.75-3.69 (m, 2H, HH-2 and HH-3), 3.60-3.53 (m, 2H, HH-2 and HH-3), 3.30 (s, 2H, H2-9); δc (125 MHz, CDCl3) 177.93 (C═O), 172.76 (C═O), 61.23 (C5), 43.12 (C9), 41.05 (C2 and C3); IR (solid, cm−1) 3290 (m), 1703 (m), 1629 (s); MS (ES−) m/z (relative intensity): 188 ([M−H], 100); Exact Mass Calcd for [C6H7NO2S2]−H requires m/z 187.9840 Found 187.9839 (ES−); m.p. 112-115° C.

Workup

  1. customAfter five minutes solvent removed in vacuo and purification by flash chromatography (10% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-1cc63dbf8ce544ee864a9fd7456317f4
Source dataset
uspto-grants-2016_03
Patent number
US09295729B2

Reaction notes

Loading…