Hydrochloric Acid → HCID 19092247, compound

HRID 487581Notes

Reaction equation

HRID 487581 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([CH2:6][CH2:7][CH:8]2[C:13](=O)NC(=O)N[C:9]2=O)=[CH:2]1.ClC1C2[C:22](=[C:23]([F:28])[CH:24]=[CH:25][CH:26]=2)[N:21]=[CH:20]C=1.[OH-].[Na+].Cl>O>[F:28][C:23]1[CH:24]=[CH:25][CH:26]=[C:13]2[C:22]=1[N:21]=[CH:20][CH:9]=[C:8]2[CH2:7][CH2:6][C:3]1[CH:4]=[CH:5][S:1][CH:2]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 27365874-Chloro-8-fluoroquinolineHCID 19092242HCID 19092242, compound

Product 1

HCID 19092247HCID 19092247, compoundYield 100.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 1.85 g of 5-[2-(3-thienyl)ethyl]-barbituric acid and 1.5 g of 4-chloro-8-fluoroquinoline was heated to 150° C. for 11/4hours, then cooled. To the cooled mixture were added 2 g of NaOH and 35 ml of water, and the mixture was heated to reflux overnight. The mixture was cooled, then acidified to pH 1.5 with concentrated HCl, and heated gently for about 11/4 hours. After cooling the mixture, the product was extracted into CH2Cl2. The CH2Cl2 solution was filtered through phase separating paper, then evaporated in vacuo, giving about 2 g of oil residue. The residue was absorbed onto silica gel and chromatographed, eluting with CH2Cl2. Fractions containing product were combined, and the title product was crystallized. Recrystallization from petroleum ether/ CH2Cl2 gave 0.68 g of the title product. M.P. 96°-97° C.

Workup

  1. temperaturecooled
  2. temperaturethe mixture was heated
  3. temperatureto reflux overnight
  4. temperatureThe mixture was cooled
  5. temperatureheated gently for about 11/4 hours
  6. temperatureAfter cooling the mixture
  7. extractionthe product was extracted into CH2Cl2
  8. filtrationThe CH2Cl2 solution was filtered through phase
  9. customseparating paper
  10. customevaporated in vacuo

Sources & evidence

ORD record
ord-664e1842f9b241ebadb8a2d3d63b981e
Source dataset
uspto-grants-1994_03
Patent number
US05296484

Reaction notes

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