Phosphoric Acid → HCID 14061074, compound

HRID 983910Notes

Reaction equation

HRID 983910 reaction equation
[F:1][C:2]1[CH:19]=[CH:18][C:5]([C:6]([N:8]2[CH2:12][CH2:11][S:10][CH:9]2[C:13]([O:15]CC)=[O:14])=[O:7])=[CH:4][CH:3]=1.[OH-].[K+].P(=O)(O)(O)O>O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([N:8]2[CH2:12][CH2:11][S:10][CH:9]2[C:13]([OH:15])=[O:14])=[O:7])=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 1004Phosphoric AcidHCID 14797Potassium HydroxideHCID 22557518Ethyl 3-(4-fluorobenzoyl)-2-thiazolidinecarboxylate

Product 1

HCID 14061074HCID 14061074, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
50 °C

Procedure

Ethyl 3-(4-fluorobenzoyl)thiazolidinecarboxylate (28.33 g, 0.1 mol) is suspended in ethanolic KOH (5% strength, 165 ml, 0.15 mol) and the mixture is subsequently heated at 50° C. (IT) for 2 h. The cooled solution is acidified (pH 2-3) with water (100 ml) and dil. phosphoric acid (8%, 150 ml). Precipitated salts are brought into solution again by addition of water (150 ml). This aqueous solution is extracted with diethyl ether (500 ml), the ethereal extracts are washed with sat. NaCl solution (100 ml), dried over Na2SO4 (sicc.) and concentrated in vacuo. The residue is crystallized from diisopropyl ether (40 ml): 24.87 g.

Workup

  1. extractionThis aqueous solution is extracted with diethyl ether (500 ml)
  2. washthe ethereal extracts are washed with sat. NaCl solution (100 ml)
  3. dry with materialdried over Na2SO4 (sicc.)
  4. concentrationconcentrated in vacuo
  5. customThe residue is crystallized from diisopropyl ether (40 ml)

Sources & evidence

ORD record
ord-c05ac3aa2eee49788a02874f5e3929bc
Source dataset
uspto-grants-2005_03
Patent number
US06867211B2

Reaction notes

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