Cysteamine → 3-(2-Aminoethylthio)-1-nonylpyrrolidine-2,5-dione

HRID 1016523Notes

Reaction equation

HRID 1016523 reaction equation
[CH2:1]([N:10]1[C:14](=[O:15])[CH:13]=[CH:12][C:11]1=[O:16])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].[SH:17][CH2:18][CH2:19][NH2:20].C(N(CC)CC)C>C(#N)C>[NH2:20][CH2:19][CH2:18][S:17][CH:13]1[CH2:12][C:11](=[O:16])[N:10]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9])[C:14]1=[O:15]

Participants

5

Reactant 3

HCID 6058CysteamineHCID 8471TriethylamineHCID 512831N-Nonylmaleimide

Product 1

HCID 5128473-(2-Aminoethylthio)-1-nonylpyrrolidine-2,5-dione

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of N-nonyl maleimide (0.01 M) prepared as described in Example 12 above, mercapto ethylamine (0.01 M) and triethylamine (0.001 M) in acetonitrile (50 ml) was stirred for 24 hours at room temperature. Acetonitrile was evaporated in vacuo and the residue obtained was triturated with ethyl acetate (25 ml). The resultant suspension was filtered and the solid washed with ethyl acetate. The solid was then dried and characterised as the desired product, N-nonyl,3-mercapto ethylamino maleimide.

Workup

  1. customprepared
  2. customAcetonitrile was evaporated in vacuo
  3. customthe residue obtained
  4. customwas triturated with ethyl acetate (25 ml)
  5. filtrationThe resultant suspension was filtered
  6. washthe solid washed with ethyl acetate
  7. customThe solid was then dried

Sources & evidence

ORD record
ord-41389818c0f841dd979c4af0486aac44
Source dataset
uspto-grants-2002_11
Patent number
US06476053B1

Reaction notes

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