Water → HCID 59498377, compound

HRID 2061016Notes

Reaction equation

Br[C:2]([CH3:14])([CH2:12]Br)[C:3](=[NH:11])[O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[CH3:15][O:16][C:17]1[CH:18]=[C:19]([OH:25])[CH:20]=[CH:21][C:22]=1[O:23][CH3:24].C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C=O)C>[CH3:15][O:16][C:17]1[CH:18]=[C:19]([O:25][CH:12]=[C:2]([CH3:14])[C:3](=[N:11][C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)[O:4][C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:20]=[CH:21][C:22]=1[O:23][CH3:24]

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of 1.0 g (2.51 mmol) of phenyl 2,3-dibromo-2-methylpropanimidate and 466 mg (3.02 mmol) of 3,4-dimethoxyphenol in 5 ml of DMF was added 2.05 g (6.29 mmol) of cesium carbonate and stirred at 70° C. for 5 hours. After cooling to room temperature, the reaction solution was poured into water and extracted with tert-butyl methyl ether. The organic layer was washed sequentially with water and a saturated NaCl, dried over anhydrous MgSO4, and concentrated under vacuum. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=5/1) to obtain 252 mg of phenyl 3-(3,4-dimethoxyphenyloxy)-2-methyl-N-phenyl-2-propenimidate (hereinafter referred to as the present compound 99) and 145 mg of 3,4-dimethoxyphenyl 3-(3,4-dimethoxyphenyloxy)-2-methyl-N-phenyl-2-propenimidate (hereinafter referred to as the present compound 100).

Workup

temperatureAfter cooling to room temperature
extractionextracted with tert-butyl methyl ether
washThe organic layer was washed sequentially with water
dry with materiala saturated NaCl, dried over anhydrous MgSO4
concentrationconcentrated under vacuum
customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=5/1)

Sources & evidence

ORD record: ord-26c74b9123dc43cab1c6b9bf6a0c3560
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08278473B2

Reaction notes

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