Hydrochloric Acid → HCID 12070577, compound

HRID 2084743Notes

Reaction equation

HRID 2084743 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][OH:10].[CH:11]([N:14]([CH:18]([CH3:20])[CH3:19])[C:15](Cl)=[O:16])([CH3:13])[CH3:12].N1C=CC=CC=1.Cl>>[CH:11]([N:14]([CH:18]([CH3:20])[CH3:19])[C:15](=[O:16])[O:10][CH2:9][CH2:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[F:1])([CH3:13])[CH3:12]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 87890Diisopropylcarbamoyl chlorideHCID 27332962-(2-Fluorophenyl)ethan-1-ol

Product 1

HCID 12070577HCID 12070577, compoundYield 98%

Conditions

Temperature
90 °C

Procedure

Under a nitrogen atmosphere, a mixture of 8.0 g (57.1 mmol) of 2-(2-fluorophenyl)ethanol, 9.34 g (57.1 mmol) of diisopropylcarbamoyl chloride and 6.93 ml (85.7 mmol) of pyridine was heated to 90° C. and stirred overnight. After cooling to room temperature, the mixture was treated with 1 N—HCl, extracted 3 times with ethyl acetate, washed with water, saturated NaHCO3, water and brine and then dried over sodium sulfate. After the solvent was distilled off, purification of the residue by silica gel chromatography gave 14.0 g of the title compound. (Yield: 98%).

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionextracted 3 times with ethyl acetate
  3. washwashed with water, saturated NaHCO3, water and brine
  4. dry with materialdried over sodium sulfate
  5. distillationAfter the solvent was distilled off
  6. custompurification of the residue by silica gel chromatography

Sources & evidence

ORD record
ord-6603474d757c404d82f1389f20b95041
Source dataset
uspto-grants-2004_04
Patent number
US06717016B2

Reaction notes

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