Acetic Acid → HCID 11749519, compound

HRID 1386127Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[N:13]=[C:12]([C:14]2[S:15][C:16](Br)=[C:17]([Br:20])[C:18]=2[CH3:19])[N:11]([CH3:22])[N:10]=1.C(O)(=O)C.O>[Zn].CCOCC>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[N:13]=[C:12]([C:14]2[S:15][CH:16]=[C:17]([Br:20])[C:18]=2[CH3:19])[N:11]([CH3:22])[N:10]=1

Participants

Conditions

Temperature: 100 °C

Procedure

Into 250-mL three-necked round bottom flask equipped with a mechanical stirrer and condenser under an atmosphere of nitrogen was added 19.26 g of 3-(2-chloro-6-fluorophenyl)-1-methyl-5-(4,5-dibromo-3-methyl-2-thienyl)-1H-1,2,4-triazole, 72 mL of acetic acid, 16 mL of water, and 3.25 g of zinc dust. The temperature of the reaction mixture was heated to 100° C. and was maintained at that temperature. After three hours the mixture was allowed to cool to room temperature and was poured into ether (500 mL) and washed with water (2×150 mL), saturated sodium bicarbonate (3×150 mL), brine, dried (Na2SO4) and the solvent removed in vacuo to give 15.4 g (96.4% yield) of the title compound as a white solid: mp 120-121° C; 1H NMR (CDCl3) δ 7.5 (s, b, 1H), 7.3-7.4 (m, 2H), 7.1 (m, 1H), 4.0 (s, 3H), 2.35 (s, 3H).

Workup

customInto 250-mL three-necked round bottom flask equipped with a mechanical stirrer and condenser under an atmosphere of nitrogen
temperaturewas maintained at that temperature
temperatureto cool to room temperature
washwashed with water (2×150 mL), saturated sodium bicarbonate (3×150 mL), brine
dry with materialdried (Na2SO4)
customthe solvent removed in vacuo

Sources & evidence

ORD record: ord-50f6bbb21926475b84dc15cb8563d206
Source dataset: uspto-grants-2001_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06265424B1

Reaction notes

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