Boron trifluoride etherate → HCID 10450370, compound

HRID 1061868Notes

Reaction equation

[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=O)=[CH:7][CH:6]=1)(=[O:4])=[O:3].Cl.[C:21]1([NH:27]N)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.B(F)(F)F.CCOCC>C(O)(=O)C>[C:14]1([C:12]2[NH:27][C:21]3[C:26]([C:11]=2[C:8]2[CH:9]=[CH:10][C:5]([S:2]([CH3:1])(=[O:4])=[O:3])=[CH:6][CH:7]=2)=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

Conditions

Temperature: 130 °C

Procedure

The mixture of 0.9 g (3.3 m mol) of 4-methylsulfonylphenyl-actophenone prepared in Example 97 and 0.5 g (3.3m mol) of phenylhydrazine hydrochloride were heated at 130° C. for 0.5 h. After cooling, 20 ml of acetic acid and 0.2 g of BF3.Et2O was added and heated to reflux for 1 h. Acetic acid was removed in vacuo, the resulting residue was suspended in water, filtered, dried and purified by column chromatography using petroleum ether/ethyl acetate 3:1 as elutant, 0.45 g of the title compound was obtained as white crystal, yield, 39.5%, m.p. 239-241° C. The data of Nuclear Magnetic Resonance shown that: 1HNMR (300 MHz, DMSO)δ: 3.24 (s, 3H, SO2CH3), 7.05-7.90 (m, 13H, Ar—H), 11.77 (s, 1H, N—H); Anal. Calcd for: C21H17NO2S: C 72.60, H 4.93, N 4.03; Found: C 72.35, H 5.03, N 4.25.

Workup

temperatureAfter cooling
temperatureheated
temperatureto reflux for 1 h
customAcetic acid was removed in vacuo
filtrationfiltered
customdried
custompurified by column chromatography
customwas obtained as white crystal
customyield

Sources & evidence

ORD record: ord-f52f348e33034f5ca81854b95dfb2c7f
Source dataset: uspto-grants-2005_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06960611B2

Reaction notes

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