Methyl iodide → HCID 58027088, compound

HRID 909306Notes

Reaction equation

[OH:1][C:2]1[CH:19]=[CH:18][CH:17]=[C:16]2[C:3]=1[O:4][C:5](=[O:23])[C:6]1[C:15]2=[CH:14][CH:13]=[C:12]2[C:7]=1[C:8]([CH3:22])=[CH:9][C:10]([CH3:21])([CH3:20])[NH:11]2.CI.[C:26](=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C(OCC)(=O)C>[CH3:26][O:1][C:2]1[CH:19]=[CH:18][CH:17]=[C:16]2[C:3]=1[O:4][C:5](=[O:23])[C:6]1[C:15]2=[CH:14][CH:13]=[C:12]2[C:7]=1[C:8]([CH3:22])=[CH:9][C:10]([CH3:20])([CH3:21])[NH:11]2

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 7-Hydroxy-2,2,4-trimethyl-1,2-dihydro-6-oxa-1-azachrysen-5-one (Reference Compound No. 1-9, 430 mg, 1.40 mmol), methyl iodide (87.2 μL, 1.40 mmol) and potassium carbonate (387 mg, 2.80 mmol) was suspended in anhydrous N,N-dimethylformamide (7 mL) and stirred at 50° C. for 3 hours. After cooling down, the reaction mixture was diluted with ethyl acetate (150 mL). The whole was washed with water (150 mL) and saturated brine (200 mL) successively, dried over anhydrous magnesium sulfate, and then the solvent was removed under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give the titled reference compound (384 mg) as a yellow solid. (Yield 85%)

Workup

temperatureAfter cooling down
washThe whole was washed with water (150 mL) and saturated brine (200 mL) successively
dry with materialdried over anhydrous magnesium sulfate
customthe solvent was removed under reduced pressure
customThe obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record: ord-d4c0c52d1a794611abdf6ce5c79ddbae
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08017775B2

Reaction notes

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