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

HRID 1258590Notes

Reaction equation

[CH3:1][S:2][C:3]1[CH:4]=[C:5]([C:9]([C:11]2[N:15]([CH3:16])[N:14]=[N:13][N:12]=2)=O)[CH:6]=[CH:7][CH:8]=1.Cl.[NH2:18][OH:19]>N1C=CC=CC=1>[OH:19][N:18]=[C:9]([C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([S:2][CH3:1])[CH:4]=1)[C:11]1[N:15]([CH3:16])[N:14]=[N:13][N:12]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To a stirred solution of [3-(methylsulfanyl)phenyl](1-methyl-1H-tetrazol-5-yl)methanone (5.62 g, 24 mmol) in dry pyridine (30 mL) was added hydroxylamine hydrochloride (4.17 g, 60 mmol). The reaction mixture was stirred at 70° C. for 5 h, then concentrated in vacuo and diluted with ethyl acetate (100 mL) and water (50 mL). The organic layer was separated, washed with water (50 mL) and dried over MgSO4. Evaporation of the solvent in vacuo afforded N-hydroxy-1-[3-(methylsulfanyl)phenyl]-1-(1-methyl-1H-tetrazol-5-yl)methanimine as a yellow solid [6.91 g, yield 99.3%; HPLC/MS: m/z=250 (M+H); logP(HCOOH)=1.98].

Workup

concentrationconcentrated in vacuo
additiondiluted with ethyl acetate (100 mL) and water (50 mL)
customThe organic layer was separated
washwashed with water (50 mL)
dry with materialdried over MgSO4
customEvaporation of the solvent in vacuo

Sources & evidence

ORD record: ord-5dd3c9ee06fe42ccb4dcbff9a3aa420d
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08466176B2

Reaction notes

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