Ammonium Chloride → 4-cyclopropyl-N-methoxy-N-methylbenzamide

HRID 554561Notes

Reaction equation

CCCCCC.C([Li])CCC.Br[C:13]1[CH:18]=[CH:17][C:16]([CH:19]2[CH2:21][CH2:20]2)=[CH:15][CH:14]=1.[CH3:22][O:23][N:24]([CH3:31])[C:25](N(OC)C)=[O:26].[Cl-].[NH4+]>C1COCC1>[CH:19]1([C:16]2[CH:17]=[CH:18][C:13]([C:25]([N:24]([O:23][CH3:22])[CH3:31])=[O:26])=[CH:14][CH:15]=2)[CH2:21][CH2:20]1

Participants

Conditions

Temperature: -78 °C

Procedure

In a nitrogen stream, an n-butyllithium hexane solution (1.6 M, 6.0 mL, 9.59 mmol) was added dropwise to an solution of 1-bromo-4-cyclopropylbenzene (1.8 g, 9.13 mmol) in anhydrous THF (30 mL) at −78° C. over 15 minutes. This solution was stirred at −78° C. for 10 minutes, and a solution of N,N′-dimethoxy-N,N′-dimethylurea (1.42 g, 9.59 mmol) in THF (15 mL) was added dropwise thereto. The reaction mixture was stirred at room temperature for 30 minutes. To the reaction mixture was added a saturated ammonium chloride aqueous solution and the mixture was extracted with ether, and the organic layer was dried over anhydrous magnesium sulfate. After filtration, the solvent was distilled under reduced pressure, and the obtained residue was purified by silica gel column chromatography [developing solution=n-hexane:ethyl acetate (4:1)] to obtain the title compound (875 mg, 95%).

Workup

stirringThe reaction mixture was stirred at room temperature for 30 minutes
extractionthe mixture was extracted with ether
dry with materialthe organic layer was dried over anhydrous magnesium sulfate
filtrationAfter filtration
distillationthe solvent was distilled under reduced pressure
customthe obtained residue was purified by silica gel column chromatography [developing solution=n-hexane:ethyl acetate (4:1)]

Sources & evidence

ORD record: ord-2804ac9e68704dd9bbf9eb34d4d0da76
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08048897B2

Reaction notes

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