Dimethylformamide → HCID 178439577, compound

HRID 1650097Notes

Reaction equation

[CH:1]([C:4]1([CH3:20])[NH:8][C:7]([C:9]2[CH:18]=[CH:17][C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:10]=2)=[N:6][C:5]1=[O:19])([CH3:3])[CH3:2].CN(C)CCN(C)C.C([Li])CCC.CN([CH:37]=[O:38])C>CCOCC.CCCCCC.O.C(O)C.C(O)(=O)C>[CH:1]([C:4]1([CH3:20])[NH:8][C:7]([C:9]2[C:18]([CH:37]=[O:38])=[CH:17][C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:10]=2)=[N:6][C:5]1=[O:19])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: -63 °C

Procedure

To a mixture of 5-isopropyl-5-methyl-2-(2-quinolyl)-2-imidazolin-4-one (3 g, 0.0112 mol) in ether (150 ml) is added tetramethylethylenediamine (3.4 g, 0.00225 mol). n-Butyllithium (17 ml, 0.027 mol) in hexane is added dropwise to the reaction mixture cooled to -63° C. An intense red color is generated and after the addition the mixture was maintained at -10° to -20° C. for 21/2 hours. Dry DMF (5 ml) was added at -10° C. and the mixture is allowed to attain room temperature, while stirring overnight. The mixture is diluted with water (75 ml) and is neutralized with acetic acid. A pale yellow solid 2.57 g (78%) is obtained with mp 226°-227° C. after crystallization* from 95% ethanol. Anal. calcd. for C17H17N3O2 : C, 69.13; H, 5.80; N, 14.23. Found: C, 68.98; H, 5.88; N, 14.25. The oxime of this aldehyde, prepared in the usual way, has mp 255°-257° C.

Workup

additionafter the addition the mixture
temperaturewas maintained at -10° to -20° C. for 21/2 hours
customto attain room temperature

Sources & evidence

ORD record: ord-14693c7ab4394e9eabfa0848e3d252c7
Source dataset: uspto-grants-1990_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04923504

Reaction notes

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