Methyl iodide → HCID 68487035, compound

HRID 1877997Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:10][C:9](=[O:11])[O:8][C:7]([C:14]([F:17])([F:16])[F:15])([CH:12]=[CH2:13])[C:6]=2[CH:18]=1.[H-].[Na+].[CH3:21]I.[Cl-].[NH4+]>CN(C=O)C.C(OCC)(=O)C.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:10]([CH3:21])[C:9](=[O:11])[O:8][C:7]([C:14]([F:15])([F:16])[F:17])([CH:12]=[CH2:13])[C:6]=2[CH:18]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred solution of 6-chloro-4-(trifluoromethyl)-4-vinyl-1,4-dihydro-2H-3,1-benzoxazin-2-one (100 mg, 0.36 mmol) in DMF (1 mL), sodium hydride (60%, 29 mg, 0.72 mmol) were added at 0° C. After the mixture was stirred at 0° C. for 30 minutes, methyl iodide (44.8 μL, 0.72 mmol) was added dropwise thereto. After the reaction solution was stirred overnight at room temperature, water was added thereto. The solution was diluted with ethyl acetate and a saturated aqueous ammonium chloride solution was added thereto. The organic layer was separated and washed with saturated brine and then dried over magnesium sulfate. After the drying agent was removed by filtration, the solvent was evaporated under reduced pressure, whereby the objective compound (107 mg, quant.) was obtained as a pale brown solid.

Workup

stirringAfter the reaction solution was stirred overnight at room temperature
customThe organic layer was separated
washwashed with saturated brine
dry with materialdried over magnesium sulfate
customAfter the drying agent was removed by filtration
customthe solvent was evaporated under reduced pressure, whereby the objective compound (107 mg, quant.)
customwas obtained as a pale brown solid

Sources & evidence

ORD record: ord-bf0b4b577389445995679dea38b65816
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08314094B2

Reaction notes

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