Methyl Ethyl Ketone → HCID 15917390, compound

HRID 1758141Notes

Reaction equation

HRID 1758141 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([Cl:8])=[CH:4][N:3]=1.[Cl:9][C:10]1[CH:11]=[CH:12][C:13]([O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[OH:23])=[N:14][CH:15]=1.C(=O)([O-])[O-].[K+].[K+].C(C(C)=O)C>O>[Cl:8][C:5]1[CH:4]=[N:3][C:2]([O:23][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[O:16][C:13]2[CH:12]=[CH:11][C:10]([Cl:9])=[CH:15][N:14]=2)=[N:7][CH:6]=1

Participants

6

Reactant 4

HCID 6569Methyl Ethyl KetoneHCID 11430Potassium CarbonateHCID 5906412,5-DichloropyrimidineHCID 15917385HCID 15917385, compound

Product 1

HCID 15917390HCID 15917390, compoundYield 76.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

With stirring, 1.80 grams (0.012 mole) of 2,5-dichloropyrimidine was added to a mixture of 2.0 grams (0.009 mole) 2-(5-chloropyridin-2-yloxy)phenol, 1.5 grams potassium carbonate, and 40 ml of methyl ethyl ketone. After the addition, the mixture was heated at reflux overnight and then poured into excess H2O. After extracting with 200 ml of ethyl ether, the extract was washed with saturated NaHCO3, H2O, brine, dried (MgSO4), filtered, and evaporated to yield a yellow solid which was recrystallized from 1-chlorobutane to give 2.3 grams of product, m.p. 108°-111°; ir (Nujol): 6.35, 6.50 (C=N), 13.20 microns; NMR (CDCl3): δ6.75 (d, 1H, pyridine ring proton), 7.35 (s, 4H, ArH), 7.65 (AB quartet, 1H, pyridine ring proton), 8.10 (d, 1H, pyridine ring proton), 8.55 (s, 2H, pyrimidine ring protons).

Workup

  1. additionAfter the addition
  2. temperaturethe mixture was heated
  3. temperatureat reflux overnight
  4. extractionAfter extracting with 200 ml of ethyl ether
  5. washthe extract was washed with saturated NaHCO3, H2O, brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customevaporated
  9. customto yield a yellow solid which
  10. customwas recrystallized from 1-chlorobutane

Sources & evidence

ORD record
ord-3c64b94e12174b92bf7918d0de5db1de
Source dataset
uspto-grants-1983_02
Patent number
US04371736

Reaction notes

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