Sodium Acetate → HCID 17854565, compound

HRID 1727886Notes

Reaction equation

[C:1]([C:4](=[CH:17][C:18]1[CH:23]=[C:22]([Cl:24])[CH:21]=[C:20]([Cl:25])[CH:19]=1)[C:5]([NH:7][CH2:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:6])(=O)[CH3:2].[CH3:26][C:27]([C:30]([NH2:32])=[NH:31])([CH3:29])[CH3:28].Cl.C([O-])(=O)C.[Na+]>CN(C=O)C>[C:27]([C:30]1[N:32]=[C:17]([C:18]2[CH:23]=[C:22]([Cl:24])[CH:21]=[C:20]([Cl:25])[CH:19]=2)[C:4]([C:5]([NH:7][CH2:8][CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:6])=[C:1]([CH3:2])[N:31]=1)([CH3:29])([CH3:28])[CH3:26]

Participants

Conditions

Temperature: 80 °C

Procedure

100 mg (0.266 mmol) of 2-acetyl-3-(3,5-dichlorophenyl)-N-(3-phenylpropyl) acrylamide was dissolved in 5 ml of DMF. 54.5 mg (0.399 mmol) of t-butyl-carbamidine-hydrochloride and 32.7 mg (0.399 mmol) of sodium acetate were added at room temperature and stirred at 80° C. for one day. After DMF was evaporated under reduced pressure, the reaction mixture was diluted with ethyl acetate and washed with saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by the silica gel chromatography (hexane/ethyl acetate=10/1 to 1/1) to obtain the title compound.

Workup

customAfter DMF was evaporated under reduced pressure
additionthe reaction mixture was diluted with ethyl acetate
washwashed with saturated aqueous sodium chloride solution
dry with materialThe organic layer was dried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by the silica gel chromatography (hexane/ethyl acetate=10/1 to 1/1)

Sources & evidence

ORD record: ord-90b3db38e3f34cc88737dfb4327a26d1
Source dataset: uspto-grants-2009_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07494989B2

Reaction notes

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