Hydroxyamine hydrochloride → N-hydroxy-1-(1-methyl-1H-tetrazol-5-yl)-1-[3-(trifluoromethoxy)phenyl]methanimine

HRID 452573

Reaction equation

[CH3:1][N:2]1[C:6]([C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([O:15][C:16]([F:19])([F:18])[F:17])[CH:10]=2)=O)=[N:5][N:4]=[N:3]1.Cl.[NH2:21][OH:22]>N1C=CC=CC=1.C(OCC)(=O)C>[OH:22][N:21]=[C:7]([C:6]1[N:2]([CH3:1])[N:3]=[N:4][N:5]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([O:15][C:16]([F:19])([F:18])[F:17])[CH:10]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To a stirred solution of (1-methyl-1H-tetrazol-5-yl)[3-(trifluoromethoxy)phenyl]methanone (5.12 g, 16.2 mmol) in dry pyridine (25 mL) was added hydroxylamine hydrochloride (2.81 g, 40.4 mmol). The mixture was stirred at 70° C. for 3 h, then left to stand overnight. After concentration of the reaction mixture in vacuo, the residue was diluted with ethyl acetate (100 mL) and washed with water (50 mL). The aqueous layer was extracted with ethyl acetate (50 mL), the combined organic layers dried (MgSO4), concentrated in vacuo and dissolved in toluene. A crystalline precipitate appeared, which was filtered off to afford N-hydroxy-1-(1-methyl-1H-tetrazol-5-yl)-1-[3-(trifluoromethoxy)phenyl]methanimine as a white solid [4.33 g, yield 92%; HPLC/MS:m/z=288 (M+H); log P(HCOOH)=2.37].

Workup

waitleft
waitto stand overnight
washwashed with water (50 mL)
extractionThe aqueous layer was extracted with ethyl acetate (50 mL)
dry with materialthe combined organic layers dried (MgSO4)
concentrationconcentrated in vacuo
dissolutiondissolved in toluene
filtrationwhich was filtered off

Sources & evidence

ORD record: ord-9a719dbbe32c4adcb817e72b8d34ec10
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08492388B2

Linked notes

Loading…