Triethylamine → HCID 18963414, compound

HRID 1975303Notes

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

Participants

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

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
extractionThe aqueous phases were extracted separately with dichloromethane
customThe combined organic phases were dried on magnesium sulfate
concentrationconcentrated by evaporation in a vacuum
customThe residue was recrystallized from 230 ml of toluene

Sources & evidence

ORD record: ord-7258a5152a76441eb4c49e33d2043267
Source dataset: uspto-grants-1994_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05286650

Reaction notes

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