Triethylamine → HCID 70550858, compound

HRID 1155673Notes

Reaction equation

HRID 1155673 reaction equation
Br.[NH2:2][CH:3]1[CH2:7][C:6](=[O:8])[N:5]([C:9]2[CH:14]=[C:13]([Cl:15])[CH:12]=[C:11]([Cl:16])[CH:10]=2)[C:4]1=[O:17].C(N(CC)CC)C.[C:25](Cl)(=O)/[CH:26]=[CH:27]/[CH3:28]>O1CCCC1>[CH2:25]([NH:2][CH:3]1[CH2:7][C:6](=[O:8])[N:5]([C:9]2[CH:10]=[C:11]([Cl:16])[CH:12]=[C:13]([Cl:15])[CH:14]=2)[C:4]1=[O:17])[CH:26]=[CH:27][CH3:28]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 643131trans-Crotonyl chlorideHCID 20537580HCID 20537580, compound

Product 1

HCID 70550858HCID 70550858, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 13.6 g of 3-amino-1-(3,5-dichlorophenyl)pyrrolidine-2,5-dione hydrobromide in 100 ml of tetrahydrofurane are added, at 0° C., 12 ml of triethylamine. Then 6 ml of crotonyl chloride are added dropwise and the reaction mixture is stirred for a further 12 hours at room temperature. The solution is then filtered and the filtrate is concentrated. The residue is purified by column chromatography over silica gel with dichloromethane/petroleum ether (85:15) as eluant. The solvent is removed and the residue is recrystallised from ethyl acetate/petroleum ether. The colourless crystals melt at 107°-110° C.

Workup

  1. filtrationThe solution is then filtered
  2. concentrationthe filtrate is concentrated
  3. customThe residue is purified by column chromatography over silica gel with dichloromethane/petroleum ether (85:15) as eluant
  4. customThe solvent is removed
  5. customthe residue is recrystallised from ethyl acetate/petroleum ether
  6. custommelt at 107°-110° C.

Sources & evidence

ORD record
ord-6bc6c6bf22ea4e8aaf0401eb2d0dea45
Source dataset
uspto-grants-1982_06
Patent number
US04332816

Reaction notes

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