Water → 6-(4-Bromophenyl)-3-(2,6-difluorophenyl)-[1,2,4]triazine

HRID 2085918Notes

Reaction equation

C(OC([NH:8][NH:9][C:10]([C:12]1[C:17]([F:18])=[CH:16][CH:15]=[CH:14][C:13]=1[F:19])=N)=O)(C)(C)C.[Br:20][C:21]1[CH:26]=[CH:25][C:24]([C:27](=O)[CH:28]=[N:29]O)=[CH:23][CH:22]=1.C([O-])(=O)C.[Na+].O>C(O)(=O)C>[Br:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2[N:8]=[N:9][C:10]([C:12]3[C:13]([F:19])=[CH:14][CH:15]=[CH:16][C:17]=3[F:18])=[N:29][CH:28]=2)=[CH:23][CH:22]=1

Participants

Conditions

Temperature: 10 °C

Procedure

A mixture of 200 mg of N′-[(2,6-difluorophenyl)-iminomethyl]-hydrazinecarboxylic acid tert-butyl ester, 114 mg of (4-bromophenyl)-oxoacetaldehyde oxime and 123 mg of sodium acetate in 1.5 ml of glacial acetic acid is heated at 10° C. for 3 h. After cooling to room temperature, the reaction mixture is poured into water and extracted with ethyl acetate. The organic phase is washed in succession with saturated sodium hydrogen carbonate solution and saturated sodium chloride solution, dried over sodium sulfate, filtered and concentrated. The residue is purified by means of flash chromatography (1% methanol in dichloromethane). In this way the title compound having a melting point of 180-181° C. is obtained.

Workup

temperatureAfter cooling to room temperature
extractionextracted with ethyl acetate
washThe organic phase is washed in succession with saturated sodium hydrogen carbonate solution and saturated sodium chloride solution
dry with materialdried over sodium sulfate
filtrationfiltered
concentrationconcentrated
customThe residue is purified by means of flash chromatography (1% methanol in dichloromethane)
customis obtained

Sources & evidence

ORD record: ord-752c34a7b7354a6fa46ce6e7d9bcd369
Source dataset: uspto-grants-2004_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06723720B2

Reaction notes

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