Cesium carbonate → HCID 18991734, compound

HRID 376061Notes

Reaction equation

HRID 376061 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:10]([CH:14]([CH3:16])[CH3:15])[CH:11]([CH3:13])[CH3:12])=[O:9])=[CH:4][C:3]=1[O:17][CH3:18].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][O:31][C:32]1[CH:37]=[CH:36][C:35]([C:38](=[NH:42])[O:39][CH2:40][CH3:41])=[CH:34][CH:33]=1>CN(C)C=O>[CH3:18][O:17][C:3]1[CH:4]=[C:5]([C:8]([N:10]([CH:11]([CH3:12])[CH3:13])[CH:14]([CH3:16])[CH3:15])=[O:9])[CH:6]=[CH:7][C:2]=1[O:1][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][O:31][C:32]1[CH:33]=[CH:34][C:35]([C:38](=[NH:42])[O:39][CH2:40][CH3:41])=[CH:36][CH:37]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 18991675HCID 18991675, compoundHCID 217472594-Hydroxy-3-methoxy-N,N-di(propan-2-yl)benzamide

Product 1

HCID 18991734HCID 18991734, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A stirred solution of 4-hydroxy-3-methoxy-N,N-bis(1-methylethyl)benzenecarboxamide (319 mg, 1.27 mmol) in 3.5 mL anhydrous N,N-dimethylformamide is treated with cesium carbonate (435 mg, 1.33 mmol) and ethyl 4-[5-bromopentoxy]benzenecarboximidoate (400 mg, 1.27 mmol) and heated at 70° C. for 1.0 hours. After cooling to room temperature, the reaction is partitioned between ethyl acetate and water and the organics washed with brine, dried over sodium sulfate and concentrated in vacuo to afford a yellow oil. This material is purified by chromatography on silica gel (22 g) with 30-75% ethyl acetate/hexanes as the eluent to afford ethyl 4-[5-[2-methoxy-4-[N,N-bis(1-methylethyl)aminocarbonyl]phenoxy]pentoxy]benzenecarboximidoate as a colorless oil.

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe reaction is partitioned between ethyl acetate and water
  3. washthe organics washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customto afford a yellow oil
  7. customThis material is purified by chromatography on silica gel (22 g) with 30-75% ethyl acetate/hexanes as the eluent

Sources & evidence

ORD record
ord-bba568bde14a4a99bea20e7060532139
Source dataset
uspto-grants-1996_01
Patent number
US05488160

Reaction notes

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