Triethylamine → HCID 22850442, compound

HRID 1975300Notes

Reaction equation

[CH:1](=[C:5]1/[C:6](=[O:11])[CH2:7][C:8](=[O:10])[NH:9]/1)\[CH:2]([CH3:4])[CH3:3].[C:12](Cl)(=[O:16])[CH2:13][CH2:14][CH3:15].C(N(CC)CC)C>ClCCl>[C:12]([O:11][C:6]1=[CH:7][C:8](=[O:10])[NH:9]/[C:5]/1=[CH:1]\[CH:2]([CH3:4])[CH3:3])(=[O:16])[CH2:13][CH2:14][CH3:15]

Participants

Conditions

Temperature: -5 °C

Procedure

31.8 g of (Z)-5-isobutylidenepyrrolidine-2,4-dione was suspended in 318 ml of dichloromethane and cooled to -5° C. Then first 23.22 g of butyryl chloride was added and then 27.32 g of triethylamine was added. After the addition the mixture was stirred another 10 minutes at 0° C., then diluted with 100 ml of dichloromethane, and washed twice with 100 ml of 5 percent NaHCO3 solution each and twice with 100 ml of 0.4M hydrochloric acid each. The aqueous phases were extracted separately with dichloromethane and the combined organic phases were dried on magnesium sulfate. After the distilling off of the solvent, the crude product (46 g) was recrystallized from hexane. The yield of the title compound was 38.8 g (84 percent of theory). The title compound had a melting point of 111° to 112° C. Other data concerning the title compound was:

Workup

additionAfter the addition the mixture
washwashed twice with 100 ml of 5 percent NaHCO3 solution each and twice with 100 ml of 0.4M hydrochloric acid each
extractionThe aqueous phases were extracted separately with dichloromethane
customthe combined organic phases were dried on magnesium sulfate
customAfter the distilling off of the solvent, the crude product (46 g) was recrystallized from hexane

Sources & evidence

ORD record: ord-1a43a081ec044787a43eec255bcd5ab2
Source dataset: uspto-grants-1994_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05286650

Reaction notes

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