Sodium hydride → 4-[5-(4-cyanophenoxy)pentyloxy]N,N-bis(1-methylethyl)benzamide

HRID 2209735Notes

Reaction equation

[OH:1][C:2]1[CH:16]=[CH:15][C:5]([C:6]([N:8]([CH:12]([CH3:14])[CH3:13])[CH:9]([CH3:11])[CH3:10])=[O:7])=[CH:4][CH:3]=1.[H-].[Na+].[C:19]([C:21]1[CH:33]=[CH:32][C:24]([O:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]Cl)=[CH:23][CH:22]=1)#[N:20]>CN(C)C=O>[C:19]([C:21]1[CH:33]=[CH:32][C:24]([O:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][O:1][C:2]2[CH:16]=[CH:15][C:5]([C:6]([N:8]([CH:12]([CH3:14])[CH3:13])[CH:9]([CH3:10])[CH3:11])=[O:7])=[CH:4][CH:3]=2)=[CH:23][CH:22]=1)#[N:20]

Participants

Conditions

Temperature: 0 °C

Procedure

A stirred solution of 4-hydroxy-N,N-bis(1-methylethyl)benzamide (2.47 g, 11.2 mmol) in 50 mL of N,N-dimethylformamide is treated with 60% sodium hydride (500 mg, 12.5 mmol). After stirring at 0° C. for 10 minutes, the reaction is treated with 5-(4-cyanophenoxy)pentyl chloride (3.25 g, 14.5 mmol) and stirred at 70° C. for 2 hours. The reaction is partitioned between ethyl acetate and water. The organic layer is washed with water and brine, dried over sodium sulfate, and concentrated in vacuo. The resulting material is purified by chromatography on silica gel (60 g) with 70-80% ethyl acetate/hexane as the eluent to afford 4-[5-(4-cyanophenoxy)pentyloxy]N,N-bis(1-methylethyl)benzamide.

Workup

stirringstirred at 70° C. for 2 hours
customThe reaction is partitioned between ethyl acetate and water
washThe organic layer is washed with water and brine
dry with materialdried over sodium sulfate
concentrationconcentrated in vacuo
customThe resulting material is purified by chromatography on silica gel (60 g) with 70-80% ethyl acetate/hexane as the eluent

Sources & evidence

ORD record: ord-8f3864f40d184da1ae340c8a6d4e2aa9
Source dataset: uspto-grants-1995_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05455274

Reaction notes

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