Hydrochloric Acid → HCID 11326643, compound

HRID 2228441Notes

Reaction equation

[CH3:1][N:2]1[C:6]([C:7]2[S:8][C:9]([C:14]#[C:15][Si](C)(C)C)=[C:10]([Cl:13])[C:11]=2[Cl:12])=[N:5][C:4]([C:20]2[C:25]([F:26])=[CH:24][CH:23]=[CH:22][C:21]=2[Cl:27])=[N:3]1.C(=O)([O-])[O-].[K+].[K+].CCOC(C)=O.CCCCC.Cl>CO.CCCCC>[CH3:1][N:2]1[C:6]([C:7]2[S:8][C:9]([C:14]#[CH:15])=[C:10]([Cl:13])[C:11]=2[Cl:12])=[N:5][C:4]([C:20]2[C:25]([F:26])=[CH:24][CH:23]=[CH:22][C:21]=2[Cl:27])=[N:3]1

Participants

Conditions

Temperature: 0 °C

Procedure

To a mixture of 1-methyl-3-(2-chloro-6-fluorophenyl)-5-(3,4-dichloro-5-(2-trimethylsilyl-ethynyl)-thien-2-yl) [1,2,4]triazole (5.0g, 10.9 mmol) in methanol (20 mL) was added potassium carbonate (1.66 g, 12 mmol) at 0° C., and the resulting off-white suspension was stirred at 0° C. for 3.5 hours. TLC analysis (10% EtOAc/Pentane) indicates complete conversion to product. The reaction was acidified with 2 N hydrochloric acid and extracted with ether (2×100 mL). The organics were combined, washed with brine, dried (sodium sulfate), filtered, and the solvent evaporated under reduced pressure to give a tan solid. Trituration with pentane affords 4.06 g (96%) of product as a tan powder: mp 145-165 (slow decomposition) 1H NMR (CDCl3) δ3.77 (s, 1H,), 4.04 (s, 3H), 7.08-7.14 (m, 1H), 7.29-7.40 (Ar-m, 2H).

Workup

extractionextracted with ether (2×100 mL)
washwashed with brine
dry with materialdried (sodium sulfate)
filtrationfiltered
customthe solvent evaporated under reduced pressure
customto give a tan solid

Sources & evidence

ORD record: ord-e486bdc3c84e41f18f61be995ede5a40
Source dataset: uspto-grants-2002_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06417187B2

Reaction notes

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