Sodium hydride → HCID 19381508, compound

HRID 2209738Notes

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][C:3]=1[O:17][CH3:18].[H-].[Na+].[C:21]([C:23]1[CH:34]=[CH:33][C:26]([O:27][CH2:28][CH2:29][CH2:30][CH2:31]Cl)=[CH:25][CH:24]=1)#[N:22]>CN(C)C=O>[C:21]([C:23]1[CH:34]=[CH:33][C:26]([O:27][CH2:28][CH2:29][CH2:30][CH2:31][O:1][C:2]2[CH:16]=[CH:15][C:5]([C:6]([N:8]([CH:9]([CH3:11])[CH3:10])[CH:12]([CH3:13])[CH3:14])=[O:7])=[CH:4][C:3]=2[O:17][CH3:18])=[CH:25][CH:24]=1)#[N:22]

Participants

Conditions

Temperature: 0 °C

Procedure

A stirred solution of 4-hydroxy-3-methoxy-N,N-bis(1-methylethyl)benzamide (1.0 g, 4.0 mmol) in 50 mL of N,N-dimethylformamide is treated with 60% sodium hydride (160 mg, 4.0 mmol). After stirring at 0° C. for 10 minutes, the reaction is treated with 4-(4-cyanophenoxy)butyl chloride (835 mg, 4.0 mmol) and stirred at 60° C. for 4 days. The reaction is partitioned between diethyl ether and water. The organic layer is washed with brine, dried over magnesium sulfate, and concentrated in vacuo. The resulting material is purified by chromatography on silica gel (30 g) with 60 % ethyl acetate/hexane as the eluent to afford 4-[4-(4-cyanophenoxy)butoxy]-3-methoxy-N,N-bis(1-methylethyl)benzamide as an oil.

Workup

stirringstirred at 60° C. for 4 days
customThe reaction is partitioned between diethyl ether and water
washThe organic layer is washed with brine
dry with materialdried over magnesium sulfate
concentrationconcentrated in vacuo
customThe resulting material is purified by chromatography on silica gel (30 g) with 60 % ethyl acetate/hexane as the eluent

Sources & evidence

ORD record: ord-0301d4a6d49f46cdab83449a008b4330
Source dataset: uspto-grants-1995_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05455274

Reaction notes

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