Hydrochloric Acid → HCID 14646887, compound

HRID 1199906Notes

Reaction equation

HRID 1199906 reaction equation
[CH2:1]([C:11]1[CH:12]=[N:13][C:14]([C:17]2[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=2)=[N:15][CH:16]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].N1C=CC=CC=1.[F:30][CH:31]([CH3:35])[C:32](Cl)=[O:33].Cl>C1C=CC=CC=1>[CH2:1]([C:11]1[CH:12]=[N:13][C:14]([C:17]2[CH:18]=[CH:19][C:20]([O:23][C:32](=[O:33])[CH:31]([F:30])[CH3:35])=[CH:21][CH:22]=2)=[N:15][CH:16]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 13741894HCID 13741894, compoundHCID 135585902Phenol, 4-(5-decyl-2-pyrimidinyl)-

Product 1

HCID 14646887HCID 14646887, compoundYield 5%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

5.4 g (173 mmol) of p-(5-decyl-2-pyrimidyl)-phenol and 1.4 g (177 mmol) of pyridine were dissolved in 30 ml of benzene, and a benzene solution of the above 2-fluoropropanoic acid chloride was added dropswise thereto at 5° C. in 15 minutes. Then, the mixture was stirred overnight at room temperature, and after the completion of the reaction, the reaction solution was poured into ice water. Then, the system was acidified with the addition of 6N-HCl and subjected to extraction with benzene. The extract benzene solution was washed with water and saline water, dried with anhydrous magnesium sulfate, and the solvent was distilled to leave 3.2 g of a crude product. The product was purified by column chromatography (eluent: hexane/acetone=10/1) to obtain 330 mg of 2-fluoropropanoic acid-p-(5-decyl-2-pyrimidyl)phenyl-ester. Yield: 5.0%.

Workup

  1. customafter the completion of the reaction
  2. extractionsubjected to extraction with benzene
  3. washThe extract benzene solution was washed with water and saline water
  4. dry with materialdried with anhydrous magnesium sulfate
  5. distillationthe solvent was distilled
  6. customto leave 3.2 g of a crude product
  7. customThe product was purified by column chromatography (eluent: hexane/acetone=10/1)

Sources & evidence

ORD record
ord-d1e67e35ab7f4e31b31d0dffdc1ea23c
Source dataset
uspto-grants-1990_02
Patent number
US04904410

Reaction notes

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