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Triethylamine → HCID 18963414, compound

HRID 1707365
Notes
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Reaction equation

HRID 1707365 reaction equation
[CH:1](=[C:8]1/[C:9](=[O:14])[CH2:10][C:11](=[O:13])[NH:12]/1)\[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:15](Cl)(=[O:19])[CH2:16][CH2:17][CH3:18].C(N(CC)CC)C>ClCCl>[CH:1](=[C:8]1/[C:9]([O:14][C:15](=[O:19])[CH2:16][CH2:17][CH3:18])=[CH:10][C:11](=[O:13])[NH:12]/1)\[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 8855Butyryl chlorideHCID 12619215HCID 12619215, compound

Product 1

HCID 18963414HCID 18963414, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of 67.0 g of (Z)-5-benzylidene pyrrolidin-2,4-dione cooled to 0° C. in 670 ml of dichloromethane, 40.0 g of butyryl chloride and then 47.1 g of triethyl amine were added and the mixture was stirred another 5 minutes at 0° C. Then the mixture washed twice with 200 ml of 5 percent NaHCO3 solution each and then twice with 200 ml of 0.5M hydrochloric acid each. The aqueous phases were extracted separately with dichloromethane. The combined organic phases were dried on magnesium sulfate and concentrated by evaporation in a vacuum. The residue was recrystallized from 230 ml of toluene. The yield of the title compound was 67.25 g (73 percent of theory). The title compound had a melting point of 139.8° to 141.5° C. Other data concerning the title compound was:

Workup

  1. washThen the mixture washed twice with 200 ml of 5 percent NaHCO3 solution each and then twice with 200 ml of 0.5M hydrochloric acid each
  2. extractionThe aqueous phases were extracted separately with dichloromethane
  3. customThe combined organic phases were dried on magnesium sulfate
  4. concentrationconcentrated by evaporation in a vacuum
  5. customThe residue was recrystallized from 230 ml of toluene

Sources & evidence

ORD record
ord-0845700202414e72ae93276162bf544e
Source dataset
uspto-grants-1994_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05352801

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes