Sodium Hydroxide → HCID 178432625, compound

HRID 1829872Notes

Reaction equation

[NH2:1][C:2]([C:21]1[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=1)([C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=1)[CH:3]([NH:5][C:6]([C:8]1[CH:13]=[N:12][CH:11]=[CH:10][N:9]=1)=O)[CH3:4].P(Cl)(Cl)(Cl)(Cl)Cl.[OH-].[Na+]>C1C=CC=CC=1>[F:20][C:17]1[CH:18]=[CH:19][C:14]([C:2]2([C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=3)[CH:3]([CH3:4])[NH:5][C:6]([C:8]3[CH:13]=[N:12][CH:11]=[CH:10][N:9]=3)=[N:1]2)=[CH:15][CH:16]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of the above-mentioned amide compound (157 mg) in benzene (4 mL) was added phosphorus pentachloride (266 mg), and the mixture was stirred at 50° C. for 3 days. After cooling to room temperature, to the reaction mixture was added 2N sodium hydroxide aqueous solution (4 ml), and the reaction mixture was stirred for an additional 30 minutes. The obtained mixture was extracted with chloroform thrice, and dried over anhydrous magnesium sulfate. The solvent was evaporated in vacuo, and the obtained residue was purified by silica gel column chromatography (C-300; hexane:ethyl acetate=1:1→1:2) to give the objective compound (100 mg).

Workup

temperatureAfter cooling to room temperature, to the reaction mixture
stirringthe reaction mixture was stirred for an additional 30 minutes
extractionThe obtained mixture was extracted with chloroform thrice
dry with materialdried over anhydrous magnesium sulfate
customThe solvent was evaporated in vacuo
customthe obtained residue was purified by silica gel column chromatography (C-300; hexane:ethyl acetate=1:1→1:2)

Sources & evidence

ORD record: ord-5ce0dee627e34eee823dbc97fd39a2c6
Source dataset: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07064142B2

Reaction notes

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