Methanamine, N-methoxy-, hydrochloride (1:1) → HCID 58136914, compound

HRID 1258520Notes

Reaction equation

[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:12]=[C:13]([S:15]([F:20])([F:19])([F:18])([F:17])[F:16])[CH:14]=1)[C:7](OCC)=[O:8])[CH3:2].Cl.[CH3:22][NH:23][O:24][CH3:25].C([Mg]Cl)(C)C>C1COCC1>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:12]=[C:13]([S:15]([F:16])([F:20])([F:17])([F:18])[F:19])[CH:14]=1)[C:7]([N:23]([O:24][CH3:25])[CH3:22])=[O:8])[CH3:2]

Participants

Conditions

Temperature: -15 °C

Procedure

Ethyl 3-ethoxy-5-(pentafluorosulfanyl)benzoate (4.8 g) was dissolved in THF (150 ml) and admixed with N,O-dimethylhydroxylamine hydrochloride (2.20 g). The mixture was cooled to approx. −15° C. under argon, and isopropylmagnesium chloride (22.5 ml, 2 M in THF) was added dropwise within 10 min. After stirring at −15° C. for 20 min, the cooling bath was removed and the mixture was stirred at RT for another 1 h. Then saturated ammonium chloride solution was added and the mixture was extracted three times with EA. The combined organic phases were dried over magnesium sulfate, filtered and concentrated. The residue was purified using silica gel (120 g cartridge, n-heptane/MtB ether gradient of 20-100% within 60 min). 2.80 g of the title compound were obtained.

Workup

customthe cooling bath was removed
stirringthe mixture was stirred at RT for another 1 h
additionThen saturated ammonium chloride solution was added
extractionthe mixture was extracted three times with EA
dry with materialThe combined organic phases were dried over magnesium sulfate
filtrationfiltered
concentrationconcentrated
customThe residue was purified
customsilica gel (120 g cartridge, n-heptane/MtB ether gradient of 20-100% within 60 min)

Sources & evidence

ORD record: ord-f426614f84ea4e31b57775494977a5f1
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08466169B2

Reaction notes

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