Maleimide → HCID 18926376, compound

HRID 128528Notes

Reaction equation

HRID 128528 reaction equation
C(O[C:6]([NH:8][CH:9]=[CH:10][CH:11]=[CH:12][CH:13]([CH3:15])[CH3:14])=O)(C)(C)C.[C:16]1(=O)[NH:20][C:19](=O)[CH:18]=[CH:17]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>C(O)C.O.O1CCCC1>[CH:13]([CH:12]1[CH:18]2[CH:17]([CH2:16][NH:20][CH2:19]2)[CH:9]([NH:8][CH3:6])[CH:10]=[CH:11]1)([CH3:15])[CH3:14]

Participants

8

Reactant 4

HCID 10935MaleimideHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 71435317HCID 71435317, compound

Product 1

HCID 18926376HCID 18926376, compoundYield 18.7%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolvent3×HCID 8028TetrahydrofuranSolvent

Procedure

50 g (0.24 mol) of 1-(tert.-butyloxycarbonylamino)-5-methyl-1,3-hexadiene are stirred together with 23 g (0.24 mol) of maleimide in 75 ml of ethanol and 75 ml of water under reflux for 24 hours. After cooling, the solid is filtered off with suction and rinsed with water to give, after drying, 56.3 g (76% of theory) of a solid of melting point 192°-195° C. 15 g (0.049 mol) are stirred together with 11 g (0.29 mol) of lithium aluminium hydride in 300 ml of tetrahydrofuran under reflux for 10 hours. After cooling, the mixture is hydrolysed with 10 ml of water, 10 ml of 10 per cent strength sodium hydroxide solution and finally 30 ml of water. The precipitate is filtered off with suction and rinsed with tetrahydrofuran and the combined filtrates are concentrated to dryness. 8.7 g of a solid are obtained and are purified by crystallisation (petroleum ether-ethyl acetate=1:5).

Workup

  1. temperatureunder reflux for 24 hours
  2. temperatureAfter cooling
  3. filtrationthe solid is filtered off with suction
  4. washrinsed with water
  5. customto give
  6. customafter drying
  7. temperatureunder reflux for 10 hours
  8. temperatureAfter cooling
  9. filtrationThe precipitate is filtered off with suction
  10. washrinsed with tetrahydrofuran
  11. concentrationthe combined filtrates are concentrated to dryness

Sources & evidence

ORD record
ord-331471647cae4a33be9f27abbea5e142
Source dataset
uspto-grants-1995_11
Patent number
US05464796

Reaction notes

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