Sodium Iodide → 3-(Boc-aminoethyloxy)benzonitrile

HRID 2414435Notes

Reaction equation

Br[CH2:2][CH2:3][NH:4][C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8].[OH:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[C:16]#[N:17].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CN(C)C=O.C(OCC)(=O)C>[C:7]([O:6][C:5]([NH:4][CH2:3][CH2:2][O:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[C:16]#[N:17])=[O:11])([CH3:10])([CH3:9])[CH3:8]

Participants

Conditions

Temperature: 50 °C

Procedure

5.85 g (29 mmol) of t-butyl (2-bromoethyl)carbamate was dissolved in 100 ml of dimethylformamide. 2.38 g (26.4 mmol) of 3-hydroxybenzonitrile, 3.04 g (53 mmol) of potassium carbonate and 4.31 g (53 mmol) of sodium iodide were added to the obtained solution, and they were stirred at 50° C. for 6 hours. After the treatment with ethyl acetate as the extraction solvent in an ordinary manner, the obtained crude product was purified by the silica gel column chromatography to obtain the title compound.

Workup

customwas purified by the silica gel column chromatography

Sources & evidence

ORD record: ord-bdc3354146e44d19a2dab911d1c15718
Source dataset: uspto-grants-2004_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06812231B2

Reaction notes

Loading…