1-Methylimidazole → HCID 118108953, compound

HRID 716162Notes

Reaction equation

CN1C=CN=C1.[CH3:7][O:8][N:9]=[CH:10][CH2:11][CH2:12][CH:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)O.CS([Cl:25])(=O)=O.C(OCC)(=O)C>C(#N)C.O>[Cl:25][CH:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:12][CH2:11][CH:10]=[N:9][O:8][CH3:7]

Participants

Conditions

Temperature: 5 °C

Procedure

0.24 mL of N-methylimidazole was added to a solution of 0.39 g of 4-(methoxyimino)-1-phenylbutan-1-ol in 4 mL of acetonitrile. Thereafter, 0.19 mL of methanesulfonyl chloride was added to the mixture at a temperature of 0° C. to 10° C., and the thus obtained mixture was then stirred at a temperature of 5° C. or lower for 1.5 hours. Thereafter, 0.24 mL of methanesulfonyl chloride was added to the reaction mixture, ethyl acetate and water were then added thereto, and the water layer was then removed. The organic layer was washed with a saturated sodium chloride aqueous solution, and was then dried over anhydrous sodium sulfate. After that, the solvent was distilled away under reduced pressure. The obtained product was purified by silica gel column chromatography (hexane/ethyl acetate=90/10 to 59/41), so as to obtain 0.07 g of (4-chloro-4-phenylbutylidene)(methoxy)amine in the form of a light yellow oily product.

Workup

additionwere then added
customthe water layer was then removed
washThe organic layer was washed with a saturated sodium chloride aqueous solution
dry with materialwas then dried over anhydrous sodium sulfate
distillationAfter that, the solvent was distilled away under reduced pressure
customThe obtained product was purified by silica gel column chromatography (hexane/ethyl acetate=90/10 to 59/41)

Sources & evidence

ORD record: ord-706f989a203d44469f67d67dceef384d
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09187514B2

Reaction notes

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