Ethanol → HCID 178458308, compound

HRID 363366Notes

Reaction equation

HRID 363366 reaction equation
[OH:1][C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[O:14][CH2:15][CH2:16][CH3:17])[N:5]=[C:4]([C:18]([OH:20])=[O:19])[CH:3]=1.[CH2:21](O)[CH3:22]>S(=O)(=O)(O)O>[OH:1][C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[O:14][CH2:15][CH2:16][CH3:17])[N:5]=[C:4]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:3]=1

Participants

4

Reactant 2

HCID 702EthanolHCID 178458309HCID 178458309, compound

Product 1

HCID 178458308HCID 178458308, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A stirred solution of 6-hydroxy-2-(2-propoxyphenyl)pyrimidine-4-carboxylic acid (1.06 g) in ethanol and concentrated sulfuric acid (0.5 ml) was heated under reflux for 3 hours. Most of the ethanol was removed under reduced pressure, then ice-water was added to the residue. The mixture was made alkaline (pH 10-11) with sodium carbonate solution and then extracted with chloroform (3×25 ml). The combined chloroform extracts were washed with water, dried (magnesium sulfate) and evaporated under reduced pressure to yield after washing with petroleum ether (b.p. 40°-60° C.) the title compound, 0.85 g, m.p. 135.5-137° C. A sample (0.4 g) was recrystallized from ethanol to yield the pure title compound, 0.22 g, m.p. 137°-8° C.

Workup

  1. temperatureunder reflux for 3 hours
  2. customMost of the ethanol was removed under reduced pressure
  3. additionice-water was added to the residue
  4. extractionextracted with chloroform (3×25 ml)
  5. washThe combined chloroform extracts were washed with water
  6. dry with materialdried (magnesium sulfate)
  7. customevaporated under reduced pressure
  8. customto yield
  9. washafter washing with petroleum ether (b.p. 40°-60° C.) the title compound, 0.85 g, m.p. 135.5-137° C
  10. customA sample (0.4 g) was recrystallized from ethanol

Sources & evidence

ORD record
ord-d973b0c369da4691a456fd4259eee4b5
Source dataset
uspto-grants-1999_02
Patent number
US05874440

Reaction notes

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