Butyl bromide → HCID 66643262, compound

HRID 1921296Notes

Reaction equation

[C:1]([C:5]1[O:9][N:8]=[C:7]([NH2:10])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].Br[CH2:12][CH2:13][CH2:14][CH3:15]>>[C:1]([C:5]1[O:9][N:8]([CH2:12][CH2:13][CH2:14][CH3:15])[C:7](=[NH:10])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

Reactant 2

HCID 8002Butyl bromide

HCID 1714733-Isoxazolamine, 5-(1,1-dimethylethyl)-

Product 1

HCID 66643262HCID 66643262, compoundYield 100%

Conditions

Temperature: 85 °C

Procedure

A mixture of 5-tert-butylisoxazol-3-amine (3.0 g, 21 mmol) and 1-bromobutane (3.5 mL, 32 mmol) was warmed to 85° C. and was allowed to stir for 70 h. The mixture was cooled to ambient temperature and was purified by column chromatography (silica gel, 60% hexanes/EtOAc) to give the title compound (4.2 g, 21 mmol, 99% yield). MS (DCI/NH3) m/z 197 (M+H)+.

Workup

temperatureThe mixture was cooled to ambient temperature
customwas purified by column chromatography (silica gel, 60% hexanes/EtOAc)

Sources & evidence

ORD record: ord-b88872d7d09f4724b1dd7477bd686317
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08173687B2

Reaction notes

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