Catechol → HCID 15917392, compound

HRID 1758140Notes

Reaction equation

HRID 1758140 reaction equation
[C:1]1([C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4])[OH:2].C(=O)([O-])[O-].[K+].[K+].Cl[C:16]1[N:21]=[CH:20][C:19]([Cl:22])=[CH:18][N:17]=1.O>CN(C)C=O>[Cl:22][C:19]1[CH:18]=[N:17][C:16]([O:2][C:1]2[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=2[OH:4])=[N:21][CH:20]=1

Participants

6

Reactant 4

HCID 289CatecholHCID 962WaterHCID 11430Potassium CarbonateHCID 5906412,5-Dichloropyrimidine

Product 1

HCID 15917392HCID 15917392, compoundYield 57.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 6.0 grams (0.055 mole) catechol and 7.0 grams of potassium carbonate stirring in 45 ml of dimethylformamide, 7.0 grams of 2,5-dichloropyrimidine was added and the mixture stirred at room temperature overnight followed by heating at 80° for 4 hours. Excess water was added to the reaction mixture, and the aqueous mixture extracted with 300 ml of ethyl ether. The ether extract was washed with H2O (2X), brine, dried (magnesium sulfate), filtered, and the solvent removed to yield a yellow oil which slowly crystallized. From a 1-chlorobutane/cyclohexane mixture, the crude solid was recrystallized to give 6.0 grams of product, m.p. 131°-139°; ir (Nujol): 2.90-3.30 (OH), 12.80, 13.30 microns.

Workup

  1. additionwas added
  2. temperatureby heating at 80° for 4 hours
  3. extractionthe aqueous mixture extracted with 300 ml of ethyl ether
  4. extractionThe ether extract
  5. washwas washed with H2O (2X), brine
  6. dry with materialdried (magnesium sulfate)
  7. filtrationfiltered
  8. customthe solvent removed
  9. customto yield a yellow oil which
  10. customslowly crystallized
  11. customFrom a 1-chlorobutane/cyclohexane mixture, the crude solid was recrystallized

Sources & evidence

ORD record
ord-85ce71479fda4e29b4c3035fb45d7cbe
Source dataset
uspto-grants-1983_02
Patent number
US04371736

Reaction notes

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