Cesium carbonate → HCID 19040962, compound

HRID 2399952Notes

Reaction equation

HRID 2399952 reaction equation
[OH:1][C:2]1[CH:16]=[C:15]([OH:17])[CH:14]=[CH:13][C:3]=1[C:4]([N:6]([CH:10]([CH3:12])[CH3:11])[CH:7]([CH3:9])[CH3:8])=[O:5].C(=O)([O-])[O-].[Cs+].[Cs+].[C:24]([C:26]1[CH:38]=[CH:37][C:29]([O:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35]Br)=[CH:28][CH:27]=1)#[N:25]>CN(C)C=O>[C:24]([C:26]1[CH:38]=[CH:37][C:29]([O:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][O:17][C:15]2[CH:14]=[CH:13][C:3]([C:4]([N:6]([CH:10]([CH3:11])[CH3:12])[CH:7]([CH3:8])[CH3:9])=[O:5])=[C:2]([OH:1])[CH:16]=2)=[CH:28][CH:27]=1)#[N:25]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 12813695HCID 12813695, compoundHCID 19040965HCID 19040965, compound

Product 1

HCID 19040962HCID 19040962, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

A solution of 2,4-dihydroxy-N,N-bis(1-methylethyl)benzamide (3 g, 12.7 mmol) in 30 mL of N,N-dimethylformamide is treated with cesium carbonate (4.97 g, 15.2 mmol), and 5-(4-cyanophenoxy)pentyl bromide (3.4 g, 12.7 mmol) and stirred at 40° C. for 24 hours. The reaction is partitioned between ethyl acetate and water, dried over sodium sulfate and concentrated in vacuo to afford a yellow foam. This material is purified by chromatography on silica gel (30 g) with 30-70% ethyl acetate/hexane as the eluent to afford 4-[5-(4-cyanophenoxy)pentyloxy]-2-hydroxy-N,N-bis(1-methylethyl)benzamide as colorless foam.

Workup

  1. customThe reaction is partitioned between ethyl acetate and water
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customto afford a yellow foam
  5. customThis material is purified by chromatography on silica gel (30 g) with 30-70% ethyl acetate/hexane as the eluent

Sources & evidence

ORD record
ord-f4fbc46c1c53490c941a0ad71b32604b
Source dataset
uspto-grants-1995_09
Patent number
US05451700

Reaction notes

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