Potassium Carbonate → 4-Benzyloxy-3-[2-(t-butoxycarbonylamino)ethoxy]benzonitrile

HRID 2414409Notes

Reaction equation

Br[CH2:2][CH2:3][NH:4][C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8].[CH2:12]([O:19][C:20]1[CH:27]=[CH:26][C:23]([C:24]#[N:25])=[CH:22][C:21]=1[OH:28])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:12]([O:19][C:20]1[CH:27]=[CH:26][C:23]([C:24]#[N:25])=[CH:22][C:21]=1[O:28][CH2:2][CH2:3][NH:4][C:5]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:11])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

Conditions

Temperature: 100 °C

Procedure

8.0 g (35.7 mmol) of t-butyl (2-bromoethyl)carbamate was dissolved in 20 ml of DMF. 4.0 g (17.7 mmol) of 4-benzyloxy-3-hydroxybenzonitrile and 7.4 g (41.3 mmol) of potassium carbonate were added to the obtained solution, and they were stirred at 100° C. for 3 hours. After the treatment with ethyl acetate as the extraction solvent in an ordinary manner, the solvent was evaporated, and the obtained residue was purified by the silica gel column chromatography to obtain the title compound.

Workup

customAfter the treatment with ethyl acetate as the extraction solvent in an ordinary manner, the solvent was evaporated
customthe obtained residue was purified by the silica gel column chromatography

Sources & evidence

ORD record: ord-2ca6df863e3140dabcfcbf1f44144f95
Source dataset: uspto-grants-2004_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06812231B2

Reaction notes

Loading…