Sodium Iodide → HCID 22267277, compound

HRID 488872Notes

Reaction equation

[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[C:7]([CH2:13][C:14]([NH:16][C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=3[C:24]([F:27])([F:26])[F:25])=[O:15])[C:8](=[O:12])[O:9]2)=[CH:4][C:3]=1[OH:34].[CH2:35]([O:37][CH2:38][CH2:39]Cl)[CH3:36].[C:41](=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CN(C=O)C.O>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[C:7]([CH2:13][C:14]([NH:16][C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=3[C:24]([F:25])([F:27])[F:26])=[O:15])[C:8](=[O:12])[O:9]2)=[CH:4][C:3]=1[O:34][CH2:36][CH2:35][O:37][CH2:38][CH2:39][CH3:41]

Participants

Conditions

Temperature: 120 °C

Procedure

A solution of 2-(7-chloro-6-hydroxy-2-oxo-4-phenyl-2H-chromen-3-yl)-N-[4-chloro-2-(trifluoromethyl)phenyl]acetamide (Example 208) (0.30 g) in DMF (5 ml) was combined with 2-chloroethyl ethyl ether (0.31 ml), potassium carbonate (0.23 g) and sodium iodide (0.15 g), and stirred at 120° C. for 30 minutes. The reaction solution was combined with water and extracted with ethyl acetate. The extract was washed with a saturated brine, and then dried over magnesium sulfate, and concentrated under reduced pressure. The resultant residue was recrystallized from ethyl acetate-diisopropyl ether to obtain the title compound as a colorless crystal (151 mg, 43%). Melting point: 170-171° C.

Workup

extractionextracted with ethyl acetate
washThe extract was washed with a saturated brine
dry with materialdried over magnesium sulfate
concentrationconcentrated under reduced pressure
customThe resultant residue was recrystallized from ethyl acetate-diisopropyl ether

Sources & evidence

ORD record: ord-0ae6dd2a4d3248d0ac215ee393b83833
Source dataset: uspto-grants-2005_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06974806B2

Reaction notes

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