Acetone → HCID 20359938, compound

HRID 1974038Notes

Reaction equation

HRID 1974038 reaction equation
[NH2:1][C:2]1[C:3]([Br:17])=[C:4]2[N:11]([OH:12])[C:10]([C:13]([F:16])([F:15])[F:14])=[N:9][C:5]2=[N:6][C:7]=1[Br:8].CI.[C:20](=O)([O-])[O-].[K+].[K+].CC(C)=O>CCOCC>[CH3:20][O:12][N:11]1[C:4]2[C:5](=[N:6][C:7]([Br:8])=[C:2]([NH2:1])[C:3]=2[Br:17])[N:9]=[C:10]1[C:13]([F:14])([F:16])[F:15]

Participants

6

Reactant 4

HCID 180AcetoneHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 20355447HCID 20355447, compound

Product 1

HCID 20359938HCID 20359938, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

6-Amino-5,7-dibromo-2-trifluoromethyl-1-hydroxy-1H-imidazo(4,5-b)pyridine (1 gram) was mixed and stirred for two hours with 2 milliliters of methyl iodide, 2 grams of potassium carbonate, and 10 milliliters of acetone. The reaction mixture was then diluted with about 80 milliliters of ether and washed with five 15-milliliter portions of water. The ether layer was dried over magnesium sulfate and filtered with carbon, and the ether removed on a rotary evaporator. The resulting 1-methoxy-6-amino-5,7-dibromo-2-(trifluoromethyl)-1H-imidazo(4,5-b)pyridine product melted at 169°-72° C. A portion was recrystallized from methanol, m.p., 177°-8° C.

Workup

  1. washwashed with five 15-milliliter portions of water
  2. dry with materialThe ether layer was dried over magnesium sulfate
  3. filtrationfiltered with carbon
  4. customthe ether removed on a rotary evaporator
  5. customA portion was recrystallized from methanol, m.p., 177°-8° C.

Sources & evidence

ORD record
ord-dd3d8089fac64e6f8d9029611f767c85
Source dataset
uspto-grants-1976_12
Patent number
US04000145

Reaction notes

Loading…