Triethylamine → Benzeneacetic acid, 4-chloro-alpha-(1-methylethyl)-

HRID 443863

Reaction equation

HRID 443863 reaction equation
FC1C=C(C=CC=1)[O:5]C1N=C(CO)C=CC=1.[CH:17]([CH:20]([C:24]1[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=1)[C:21](Cl)=[O:22])([CH3:19])[CH3:18].C(N(CC)CC)C>CCOCC>[Cl:30][C:27]1[CH:28]=[CH:29][C:24]([CH:20]([CH:17]([CH3:19])[CH3:18])[C:21]([OH:5])=[O:22])=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 41780012-(4-Chlorophenyl)-3-methylbutanoyl chlorideHCID 62240382HCID 62240382, compound

Product 1

HCID 16197Benzeneacetic acid, 4-chloro-alpha-(1-methylethyl)-

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 1.8 grams (0.0078 mole) of cyano(6-(3-fluorophenoxy)-2-pyridine methanol and 2.4 grams (0.0098 mole) of 2-isopropyl-2-(4-chlorophenyl)-acetic acid chloride in 50 milliliters of anhydrous ether was added 3 milliliters of triethylamine. A white precipitate separated out immediately. The reaction mixture was stirred at room temperature for one-half (1/2) hour. The mixture was successively washed with water, dilute hydrochloric acid, dilute sodium hydroxide, dilute sodium bicarbonate, dilute hydrochloric acid and water and thereafter dried over anhydrous magnesium sulfate and concentrated under vacuo to give 3.6 grams of 4-chloro-α-(1-methylethyl)benzeneacetic acid:cyano(6-(3-fluorophenoxy)-2-pyridinyl)methyl ester product as a viscous yellow oil having a refractive index of nD25 =1.5560. The structure of the product was confirmed by its nuclear magnetic resonance spectrum (NMR). In addition, upon analysis, the product was found to have carbon, hydrogen and nitrogen contents of 65.52, 4.74 and 6.18 percent, respectively, as compared with theoretical contents of 65.66, 4.59 and 6.38 percent, respectively, as calculated for the above-named compound (Compound No. 3).

Workup

  1. customA white precipitate separated out immediately
  2. washThe mixture was successively washed with water, dilute hydrochloric acid, dilute sodium hydroxide, dilute sodium bicarbonate, dilute hydrochloric acid and water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under vacuo

Sources & evidence

ORD record
ord-69b7cd8f46d64cb89b0054b747908ed0
Source dataset
uspto-grants-1981_04
Patent number
US04262001

Linked notes

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