N,N-Dimethylcyclopropanecarboxamide → HCID 24720860, compound

HRID 446047Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:17])([CH3:16])[C:9]2[O:10][CH2:11][C:12]([CH3:15])([CH3:14])[N:13]=2)=[CH:4][CH:3]=1.C([Li])CCC.CN(C)[C:25]([CH:27]1[CH2:29][CH2:28]1)=[O:26]>C1COCC1>[CH:27]1([C:25](=[O:26])[C:2]2[CH:7]=[CH:6][C:5]([C:8]([CH3:17])([CH3:16])[C:9]3[O:10][CH2:11][C:12]([CH3:15])([CH3:14])[N:13]=3)=[CH:4][CH:3]=2)[CH2:29][CH2:28]1

Participants

Conditions

Temperature: -78 °C

Procedure

A solution of 4-bromo-α,α-dimethyl-α-(4,4-dimethyloxazolin-2-yl)toluene, prepared according to Example 2, (10.0 g. 0.0338 mole) in 400 mL THF was cooled to −78° C., n-butyllithium (16 mL, 0.042 mole) was added via syringe, and the mixture was stirred at −78° C. for 30 minutes. While keeping the temperature below −75° C., N,N-dimethyl cyclopropylcarboxylic acid amide (11.5 g, 0.102 mole) in 30 mL THF was added dropwise, and the mixture was stirred at −78° C. for 30 minutes. The mixture was allowed to warm to −15° C., and was quenched with water. The product was extracted with methylene chloride, washed with saturated NaCl solution, dried over Na2SO4, and concentrated. The residue was cooled to 0° C., treated with minimal acetonitrile, and filtered, to afford 6.95 g of 4-(cyclopropyl-oxo-methyl)-α,α-dimethyl-α-(4,4-dimethyloxazolin-2-yl)toluene as a white solid (72%).

Workup

additionwas added dropwise
stirringthe mixture was stirred at −78° C. for 30 minutes
temperatureto warm to −15° C.
customwas quenched with water
extractionThe product was extracted with methylene chloride
washwashed with saturated NaCl solution
dry with materialdried over Na2SO4
concentrationconcentrated
temperatureThe residue was cooled to 0° C.
additiontreated with minimal acetonitrile
filtrationfiltered

Sources & evidence

ORD record: ord-777c80c668ed4281abd7e165b30cedb2
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08476445B2

Reaction notes

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