Dimethylformamide → HCID 178516667, compound

HRID 1490263Notes

Reaction equation

F[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]([F:11])([F:10])[F:9])[C:3]=1[C:12](=[O:14])[CH3:13].[C:15](=[S:17])=[S:16].CN(C)C=O.[H-].[Na+]>C1C=CC=CC=1.O.C(O)(=O)C>[OH:14][C:12]1[C:3]2[C:2](=[CH:7][CH:6]=[CH:5][C:4]=2[C:8]([F:11])([F:10])[F:9])[S:17][C:15](=[S:16])[CH:13]=1

Participants

Conditions

Temperature: 125 °C

Procedure

A mixture of 2'-fluoro-6'-(trifluoro-methyl)acetophenone (3.0 g, 14.5 mmol), carbon disulfide (1.5 mL, 26.7 mmol) and dimethylformamide (DMF) (12.5 mL) in benzene at 15°-25° C. is treated portion-wise with a 60% dispersion of sodium hydride in mineral oil (1.15 g, 28.8 mmol NaH) over a 1.5 hour period, stirred for 0.5 hour, heated at 125° C. for 1 hour, cooled to room temperature and diluted with water. The resultant mixture is treated with acetic acid and extracted with ether. The aqueous phase is acidified to pH 3 with HCl and extracted with ethyl acetate. The ethyl acetate extracts are combined, washed sequentially with water and brine, dried over MgSO4 and concentrated in vacuo to give an orange oil residue. The residue is crystallized from diethyl ether/hexanes to give the title product as a white solid, 3.0 g (79% y), mp 142°-144° C., identified by IR, 1HNMR, 19FNMR and mass spectral analyses.

Workup

temperaturecooled to room temperature
extractionextracted with ether
extractionextracted with ethyl acetate
washwashed sequentially with water and brine
dry with materialdried over MgSO4
concentrationconcentrated in vacuo
customto give an orange oil residue
customThe residue is crystallized from diethyl ether/hexanes

Sources & evidence

ORD record: ord-fadc7981f0114c93af3a2b6c0b25d833
Source dataset: uspto-grants-1997_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05681968

Reaction notes

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