Hydroxyamine hydrochloride → 6-[(2-Chloro-alpha,alpha,alpha,6-tetrafluoro-p-tolyl)oxy]-alpha-methyl-1h-benzotriazole-1-acetaldehyde oxime

HRID 963662Notes

Reaction equation

CO[CH:3](OC)[CH:4]([CH3:27])[N:5]1[C:9]2[CH:10]=[C:11]([O:14][C:15]3[CH:20]=[C:19]([F:21])[C:18]([C:22]([F:25])([F:24])[F:23])=[C:17]([Cl:26])[CH:16]=3)[CH:12]=[CH:13][C:8]=2[N:7]=[N:6]1.Cl.[NH2:31][OH:32]>C(O)(=O)C.O.N1C=CC=CC=1.C(O)C>[Cl:26][C:17]1[CH:16]=[C:15]([O:14][C:11]2[CH:12]=[CH:13][C:8]3[N:7]=[N:6][N:5]([CH:4]([CH3:27])[CH:3]=[N:31][OH:32])[C:9]=3[CH:10]=2)[CH:20]=[C:19]([F:21])[C:18]=1[C:22]([F:25])([F:24])[F:23]

Participants

Conditions

Temperature: 70 °C

Procedure

A solution of 6-[(2-chloro-α,α,α,6-tetrafluoro-p-tolyl) oxy]-α-methyl-1H-benzotriazole-1-acetaldehyde dimethyl acetal (23.0 g, 0.053 mole) in acetic acid is treated with 54 ml of 2.5N H2 SO4 and stirred at 70° C. for 12 hours. A 15 ml portion of the reaction solution is diluted to a total volume of 100 ml with water, the resulting precipitate is separated, washed with water, treated with a solution of hydroxylamine hydrochloride (1.0 g, 0.014 mole) in pyridine and ethanol, heated at 85° C. for several hours, cooled and concentrated in vacuo to give a solid residue. Recrystallization from aqueous ethanol, ethanol and toluene gives the title compound mp 148°-151° C., identified by elemental and NMR analyses.

Workup

customthe resulting precipitate is separated
washwashed with water
temperatureheated at 85° C. for several hours
temperaturecooled
concentrationconcentrated in vacuo
customto give a solid residue
customRecrystallization from aqueous ethanol, ethanol and toluene

Sources & evidence

ORD record: ord-b573b43fe6a841689b47137525354f27
Source dataset: uspto-grants-1998_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05763615

Reaction notes

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