Sodium Acetate → But-3-enylaminomaleimide

HRID 929395Notes

Reaction equation

HRID 929395 reaction equation
Cl.[CH2:2]([NH2:6])[CH2:3][CH:4]=[CH2:5].C([O-])(=O)C.[Na+].Br[C:13]1[C:14]([NH:16][C:17](=[O:19])[CH:18]=1)=[O:15]>CO>[CH2:2]([NH:6][C:13]1[C:14]([NH:16][C:17](=[O:19])[CH:18]=1)=[O:15])[CH2:3][CH:4]=[CH2:5]

Participants

5

Reactant 3

HCID 517045Sodium AcetateHCID 118195503-bromo-2,5-dihydro-1H-pyrrole-2,5-dioneHCID 12363007But-3-en-1-amine hydrochloride

Product 1

HCID 66927418But-3-enylaminomaleimideYield 76%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To 3-butenylamine hydrochloride (200 mg, 1.12 mmol) and sodium acetate (184 mg, 2.24 mmol) in methanol (15 mL) was added bromomaleimide (200 mg, 1.12 mmol) dropwise in methanol (15 mL). After 10 minutes, solvent was removed in vacuo and purification by flash chromatography (10% ethyl acetate in petroleum ether) afforded the desired compound as a bright yellow waxy solid (142 mg, 0.85 mmol) in 76% yield. δH (500 MHz, CDCl3) 7.10 (s, 1H, NH), 5.77 (tdd, 1H, J=6.9, 10.7 and 17.4, H-2), 5.38 (s, 1H, NH), 5.18-5.15 (m, 2H, H2-1), 4.83 (d, 1H, J=1.3, H-6), 3.24 (t, 2H, J=6.7, H2-4), 2.40 (dtd, 2H, J=1.2, 6.8 and 6.9, H2-3); δC (125 MHz, CDCl3) 171.94 (C═O), 167.45 (C═O), 149.53 (C5), 133.89 (C2), 118.51 (C1), 85.80 (C6), 43.30 (C4), 32.68 (C3); IR (solid, cm−1) 3290 (m), 1703 (m), 1629 (s); MS (ES−) m/z (relative intensity): 165 ([M−H], 100); Exact Mass Calcd for [C8H10N2O2]−H requires m/z 165.0659 Found 165.0664 (ES−); m.p. 68-76° C.; UV (Acetonitrile) ε241=8300 and ε348=6100 cm−1M−1 d3.

Workup

  1. customsolvent was removed in vacuo and purification by flash chromatography (10% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-6dc7424343c6458980cbe701d06c7527
Source dataset
uspto-grants-2016_03
Patent number
US09295729B2

Reaction notes

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