Hydrochloric Acid → HCID 14419502, compound

HRID 1199905Notes

Reaction equation

HRID 1199905 reaction equation
[F:1][CH:2]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])[C:3]([OH:5])=[O:4].S(Cl)(Cl)=O.C1N2CCN(CC2)C1.[CH2:24]([C:34]1[CH:35]=[N:36][C:37]([C:40]2[CH:45]=[CH:44][C:43](O)=[CH:42][CH:41]=2)=[N:38][CH:39]=1)[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33].[H-].[Na+].Cl>C1C=CC=CC=1>[CH2:24]([C:34]1[CH:39]=[N:38][C:37]([C:40]2[CH:45]=[CH:44][C:43]([O:4][C:3](=[O:5])[CH:2]([F:1])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])=[CH:42][CH:41]=2)=[N:36][CH:35]=1)[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33]

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 9237DabcoHCID 24386Thionyl ChlorideHCID 24758Sodium hydrideHCID 144195012-Fluorooctanoic acidHCID 135585902Phenol, 4-(5-decyl-2-pyrimidinyl)-

Product 1

HCID 14419502HCID 14419502, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
90 °C

Procedure

More specifically, 0.24 mg (1.5 mmol) of 2-fluorooctanoic acid was added to 2 ml of thionyl chloride and the mixture was refluxed at 90° C. for 2 hours. Then, the excess of thionyl chloride was distilled off, and a preliminarily prepared solution of 0.34 g (3.0 mmol) of triethylenediamine and 0.47 g (1.5 mmol) of 5-n-decyl-2-(p-hydroxyphenyl)pyrimidine in 5 ml of dry benzene was quickly added thereto, followed by 2 hours of stirring at 50° C. Thereafter, 0.06 g (1.5 mmol) of sodium hydride (60%) was added, and the mixture was further refluxed for 2 hours at 90° C. After the reaction, 2N-hydrochloric acid was added to the system, which was then subjected to extraction with benzene. The extract was dried, subjected to distillation of the solvent and purified by column chromatography with benzene to obtain 0.44 g (0.96 mmol) of 5-n-decyl-2-[4-(2-fluorooctanoyloxy)phenyl]pyrimidine. Yield: 64%

Workup

  1. distillationThen, the excess of thionyl chloride was distilled off
  2. temperaturethe mixture was further refluxed for 2 hours at 90° C
  3. additionwas added to the system, which
  4. extractionwas then subjected to extraction with benzene
  5. customThe extract was dried
  6. distillationsubjected to distillation of the solvent
  7. custompurified by column chromatography with benzene

Sources & evidence

ORD record
ord-b6b8cd297f2e42569873dc4d4562d6b6
Source dataset
uspto-grants-1990_02
Patent number
US04904410

Reaction notes

Loading…