Methanesulfonic Acid → HCID 57524351, compound

HRID 623802Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[N:12]=[CH:11][N:10](/[CH:13]=[CH:14]\[C:15]([NH:17][NH2:18])=[O:16])[N:9]=2)[CH:5]=[CH:6][CH:7]=1.[CH:19](OCC)(OCC)OCC.CS(O)(=O)=O>C(OCC)(=O)C.CCCCCC>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[N:12]=[CH:11][N:10](/[CH:13]=[CH:14]\[C:15]3[O:16][CH:19]=[N:18][N:17]=3)[N:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 80 °C

Procedure

In a 3-neck 25 mL round-bottomed flask, (Z)-3-(3-(3-chlorophenyl)-1H-1,2,4-triazol-1-yl)acrylohydrazide (0.180 g, 1.0 eq.), triethyl orthoformate (0.2006 g, 1.9 eq.) and Methane sulphonic acid (0.009 g, 0.1 eq.) was mixed. Reaction was carried out under N2 atmosphere. Reaction mixture was refluxed at 80° C. for 1 h. Completion of the reaction was monitored on TLC using ethyl acetate:n-hexane (1:1) as mobile phase. The resulting reaction mass was poured in ice-water slurry (50 mL) and extracted with ethylacetate (3×20 mL). Organic layer was washed with brine solution followed by drying using anhydrous sodium sulphate. Organic layer was concentrated under reduced pressure to afford 0.150 g of crude compound which was further purified using column chromatography to afford 0.045 g pure compound (Yield 24.2%): 1H NMR (400 MHz, CDCl3) δ 10.21 (S, 1H), 8.5 (S, 1H), 8.18 (S, 1H), 8.05-8.06 (t, 1H), 7.50-7.53 (d, J=10.8 Hz, 1H), 7.40-7.43 (t, 1H), 6.25-6.27 (d, J=11.2 Hz, 1H): LCMS for C12H8ClN5O [M+1]+ 273.68 found 273.80 at 3.336 min.

Workup

customReaction
customReaction mixture
customThe resulting reaction mass
extractionextracted with ethylacetate (3×20 mL)
washOrganic layer was washed with brine solution
customby drying
concentrationOrganic layer was concentrated under reduced pressure
customto afford 0.150 g of crude compound which
customwas further purified

Sources & evidence

ORD record: ord-207159a8537f48b583e61370126220ed
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09303000B2

Reaction notes

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