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

HRID 2209735
Notes
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Reaction equation

HRID 2209735 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 193815104-((5-Chloropentyl)oxy)benzonitrileHCID 218414724-hydroxy-N,N-bis(propan-2-yl)benzamide

Product 1

HCID 193814984-[5-(4-cyanophenoxy)pentyloxy]N,N-bis(1-methylethyl)benzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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

  1. stirringstirred at 70° C. for 2 hours
  2. customThe reaction is partitioned between ethyl acetate and water
  3. washThe organic layer is washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes