Chloroform → HCID 19040993, compound

HRID 2209730Notes

Reaction equation

HRID 2209730 reaction equation
[C:1]([C:3]1[CH:31]=[CH:30][C:6]([O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][C:14]2[CH:28]=[CH:27][C:17]([C:18]([N:20]([CH:24]([CH3:26])[CH3:25])[CH:21]([CH3:23])[CH3:22])=[O:19])=[C:16]([OH:29])[CH:15]=2)=[CH:5][CH:4]=1)#[N:2].[OH-:32].[Na+].C(Cl)(Cl)Cl>CC(C)=O>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][C:14]2[CH:28]=[CH:27][C:17]([C:18]([N:20]([CH:24]([CH3:25])[CH3:26])[CH:21]([CH3:23])[CH3:22])=[O:19])=[C:16]([CH:15]=2)[O:29][C:17]([CH3:27])([CH3:16])[C:18]([OH:19])=[O:32])=[CH:30][CH:31]=1)#[N:2]

Participants

5

Reactant 3

HCID 6212ChloroformHCID 14798Sodium HydroxideHCID 19040962HCID 19040962, compound

Product 1

HCID 19040993HCID 19040993, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

A stirred solution of 4-[5-(4-cyanophenoxy)pentyloxy]-2-hydroxy-N,N-bis(1-methylethyl)benzamide (5.7 g, 13.4 mmol) in 50 mL of acetone is treated with sodium hydroxide (5.4 g, 134 mmol) and heated to reflux. The reaction is treated slowly with chloroform (1.4 mL, 17.4 mmol) in 150 mL of acetone and refluxed for 4 hours. The reaction is concentrated in vacuo and the residue is partitioned between ethyl acetate and 1N hydrochloric acid. The organic phase is washed with brine, dried over magnesium sulfate, and concentrated in vacuo. The resulting material is purified by chromatography on silica gel (200 g) with 0-10% methanol/ethyl acetate as the eluent to afford 2-[5-[5-(4-cyanophenoxy)pentyloxy]-2-[N,N -bis(1-methylethyl)aminocarbonyl]phenoxy]-2-methylpropanoic acid as a colorless foam.

Workup

  1. temperatureheated to reflux
  2. temperaturerefluxed for 4 hours
  3. concentrationThe reaction is concentrated in vacuo
  4. customthe residue is partitioned between ethyl acetate and 1N hydrochloric acid
  5. washThe organic phase is washed with brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe resulting material is purified by chromatography on silica gel (200 g) with 0-10% methanol/ethyl acetate as the eluent

Sources & evidence

ORD record
ord-8c7863ff7f1e44f38fdd20e375cb48bb
Source dataset
uspto-grants-1995_10
Patent number
US05455274

Reaction notes

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