Imidazole → 6-methyl-1H-inden-1,2(3H)-dione 2-{O-[tert-butyl(dimethyl)silyl]oxime}

HRID 1893512Notes

Reaction equation

CN(C)C=O.[CH3:6][C:7]1[CH:15]=[C:14]2[C:10]([CH2:11][C:12](=[N:17][OH:18])[C:13]2=[O:16])=[CH:9][CH:8]=1.N1C=CN=C1.[Si:24](Cl)([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25]>O>[Si:24]([O:18][N:17]=[C:12]1[CH2:11][C:10]2[C:14](=[CH:15][C:7]([CH3:6])=[CH:8][CH:9]=2)[C:13]1=[O:16])([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25]

Participants

Conditions

Temperature: 95 °C

Procedure

To N,N-dimethylformamide (50 ml) were added at room temperature the compound (4.36 g, 24.9 mmol) obtained in step A, imidazole (5.10 g, 74.7 mmol) and tert-butyldimethylsilyl chloride (5.60 g, 37.4 mmol), and the mixture was stirred at 95° C. for 2 hr. After cooling to room temperature, water was added to the reaction solution with stirring and the precipitated solid was filtered, washed with water, and dried under reduced pressure to give the title compound (6.00 g, yield 83%) as a pale-bistered solid.

Workup

temperatureAfter cooling to room temperature
stirringwith stirring
filtrationthe precipitated solid was filtered
washwashed with water
customdried under reduced pressure

Sources & evidence

ORD record: ord-993fdb9e18814b24aa804676ec771d1c
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08513235B2

Reaction notes

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