Hydroxyamine hydrochloride → tert-Butyl N-allyl-N-[2-hydroxyimino-2-(2-thienyl)ethyl]carbamate

HRID 470220Notes

Reaction equation

[CH2:1]([N:4]([CH2:12][C:13](=O)[C:14]1[S:15][CH:16]=[CH:17][CH:18]=1)[C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8])[CH:2]=[CH2:3].Cl.[NH2:21][OH:22].C([O-])(=O)C.[Na+]>C(O)C>[CH2:1]([N:4]([CH2:12][C:13](=[N:21][OH:22])[C:14]1[S:15][CH:16]=[CH:17][CH:18]=1)[C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8])[CH:2]=[CH2:3]

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of tert-butyl N-allyl-N-[2-oxo-2-(2-thienyl)ethyl]carbamate (15.2 g, 54.0 mmol), hydroxylamine hydrochloride (5.63 g, 81.0 mmol) and sodium acetate (6.65 g 81.0 mmol) in ethanol (216 mL) is stirred at 70° C. for 18 hours. The reaction is cooled and the solvent removed under reduced pressure. The residue is diluted water (100 mL) and extracted with dichloromethane. The organic layers are combined dried over sodium sulfate, filtered and concentrated under reduced pressure to give the crude title compound as a mixture of E and Z isomers, which is used without further purification (16 g, >98%): ES/MS (m/e): 197 (M+H-100).

Workup

temperatureThe reaction is cooled
customthe solvent removed under reduced pressure
extractionextracted with dichloromethane
dry with materialThe organic layers are combined dried over sodium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-0e06c1bd3fb641a39ab2d5bdf22bc350
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08629270B2

Reaction notes

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