Toluene → 3-(9-bromo-4,5-dihydrobenzo[b]thieno[2,3-d]oxepin-2-yl)-4-(2,4-difluorophenyl)-4H-1,2,4-triazole

HRID 627996

Reaktionsgleichung

[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:14][CH2:13][CH2:12][C:11]3[CH:10]=[C:9]([C:15]([NH2:17])=O)[S:8][C:7]=3[C:6]=2[CH:18]=1.CO[CH:21](OC)[N:22](C)C.C1(C)C=CC=CC=1.Cl.[F:35][C:36]1[CH:41]=[C:40]([F:42])[CH:39]=[CH:38][C:37]=1[NH:43]N>C(O)(=O)C.ClCCl.O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:14][CH2:13][CH2:12][C:11]3[CH:10]=[C:9]([C:15]4[N:43]([C:37]5[CH:38]=[CH:39][C:40]([F:42])=[CH:41][C:36]=5[F:35])[CH:21]=[N:22][N:17]=4)[S:8][C:7]=3[C:6]=2[CH:18]=1

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

A mixture of 9-bromo-4,5-dihydro-6-oxa-1-thia-benzo[e]azulene-2-carboxylic acid amide (340 mg), dimethylformamide dimethyl acetal (3 ml) and toluene (2.5 mL) was heated to 100° C. for 16 hours. The solvent was then reduced in vacuo and dissolved in acetic acid (3 ml) and water (0.3 mL) and to this was added 2,4-difluorophenylhydrazine hydrochloride (265 mg). The reaction mixture was heated to 100° C. for 3 hours. The reaction mixture was then cooled, and then diluted with dichloromethane, washed with sodium carbonate solution, dried (MgSO4) and the solvent removed in vacuo. Purification using flash chromatography yielded 293. NMR: (CDCl3): 3.15 (2H, t), 4.31 (2H, t), 6.82 (1H, d), 6.86 (1H, s), 7.08-7.13 (2H, m), one proton under chloroform peak, 7.72 (1H, s), 8.10 (1H, s)

Aufarbeitung

temperatureThe reaction mixture was heated to 100° C. for 3 hours
temperatureThe reaction mixture was then cooled
washwashed with sodium carbonate solution
dry with materialdried (MgSO4)
customthe solvent removed in vacuo
customPurification

Quellen und Nachweise

ORD-Eintrag: ord-b5f837d48fb44bcaa26e004513a3a65a
Quelldatensatz: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09309265B2

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