Acetic Acid → HCID 13713505, compound

HRID 542779Notes

Reaction equation

HRID 542779 reaction equation
BrBr.[Cl:3][C:4]1[CH:21]=[CH:20][C:7]([O:8][C:9]([CH3:19])([CH3:18])[C:10](=[O:17])[CH2:11][N:12]2[CH:16]=[N:15][CH:14]=[N:13]2)=[CH:6][CH:5]=1.[Cl:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=1.C(N(CC)CC)C.C(O)(=[O:38])C>O>[Cl:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([O:38][CH:11]([N:12]2[CH:16]=[N:15][CH:14]=[N:13]2)[C:10](=[O:17])[C:9]([O:8][C:7]2[CH:6]=[CH:5][C:4]([Cl:3])=[CH:21][CH:20]=2)([CH3:18])[CH3:19])[N:24]=1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 79772-ChloropyridineHCID 8471TriethylamineHCID 24408BromineHCID 13073535HCID 13073535, compound

Product 1

HCID 13713505HCID 13713505, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

12.8 g (approx. 4.2 ml, that is 0.08 mol) of bromine are added dropwise to 22.4 g (0.08 mol) of 3-(4-chlorophenoxy)-3-methyl-1-(1,2,4-triazol-1-yl)-butan-2-one in 100 ml of glacial acetic acid at 50° C., while stirring. Thereafter, stirring is continued until the mixture has become completely decolourised (approx. 20 minutes), the mixture is poured into water and extracted with methylene chloride, and the organic phase is washed with sodium bicarbonate until it gives a neutral reaction. Thereafter, the solvent is removed in vacuo, and the residue is dissolved in 100 ml of acetonitrile. A homogeneous solution of 11.6 g (0.1 mol) of chloropyridine and 16 ml (0.1 mol) of triethylamine is added, all at once, to the stirred solution. When the exothermic reaction has died down, the mixture is kept at the boil for a further 30 minutes and then poured into water and extracted with methylene chloride. The organic phase is washed twice with dilute sodium hydroxide solution, and freed from the solvent, and the oil which remains is recrystallised from a small amount of methanol. 12.4 g (that is 31% of theory) of 1-(2-chloropyrid-6-yloxy)-3-(4-chlorophenoxy)-3-methyl-1-(1,2,4-triazol-1-yl)-butan-2-one of melting point 101° C. are obtained.

Workup

  1. stirringThereafter, stirring
  2. custom(approx. 20 minutes)
  3. extractionextracted with methylene chloride
  4. washthe organic phase is washed with sodium bicarbonate until it
  5. customgives
  6. customa neutral reaction
  7. customThereafter, the solvent is removed in vacuo
  8. dissolutionthe residue is dissolved in 100 ml of acetonitrile
  9. customWhen the exothermic reaction
  10. extractionextracted with methylene chloride
  11. washThe organic phase is washed twice with dilute sodium hydroxide solution
  12. customthe oil which remains is recrystallised from a small amount of methanol

Sources & evidence

ORD record
ord-b43a941778bc41dfad4ab5c6e67e9f29
Source dataset
uspto-grants-1987_04
Patent number
US04659723

Reaction notes

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