Phenacyl bromide → HCID 19696491, compound

HRID 1789208Notes

Reaction equation

HRID 1789208 reaction equation
[OH:1][CH2:2][C:3]1[C:4]([NH2:9])=[N:5][CH:6]=[CH:7][CH:8]=1.Br[CH2:11][C:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=O>C(O)C>[OH:1][CH2:2][C:3]1[C:4]2[N:5]([CH:11]=[C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[N:9]=2)[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 6259Phenacyl bromideHCID 11159325(2-Aminopyridin-3-yl)methanol

Product 1

HCID 19696491HCID 19696491, compoundYield 62.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1.24 g (10 mmole) of 3-hydroxymethyl-2-pyridinamine and 2.0 g (10 mmole) of α-bromoacetophenone in 25 ml of ethanol was stirred at room temperature. After 18 hours the resultant solid was collected, washed with ethano, and dissolved in water. The solution was made basic with aqueous potassium carbonate and extracted with dichloromethane. The organic layer was dried over magnesium sulfate, filtered, and concentrated in vacuo. The residue was triturated with diethyl ether, collected by filtration, washed with diethyl ether, and air dried to yield 1.4 g of 8-hydroxymethyl-2-phenylimidazo[1,2-a]pyridine, as confirmed by the nmr and infrared spectra and by elemental analysis. [Calcd. for C14H12N2O2 : C, 74.98; H, 5.39; N, 12.49. Found: C, 74.68; H, 5.39; N, 12.40.] A mixture of 871 mg (5.8 mmole) of 2-mercaptobenzimidazole and 1.3 g (5.8 mmole) of 8-hydroxymethyl-2-phenylimidazo[1,2-a]pyridine was dissolved in 10 ml of 47% aqueous hydrobromic acid and 10 ml of acetic acid and heated to reflux. After being cooled to room temperature, the mixture was poured into water, made alkaline with potassium carbonate, and extracted with dichloromethane. The organic layer was dried over magnesium sulfate, filtered, and concentrated in vacuo. Trituration of the residue with diethyl ether yielded 1.8 g of the analytically pure title compound. Structure assignment was supported by the nmr and infrared spectra and by elemental analysis.

Workup

  1. customAfter 18 hours the resultant solid was collected
  2. washwashed with ethano
  3. dissolutiondissolved in water
  4. extractionextracted with dichloromethane
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was triturated with diethyl ether
  9. filtrationcollected by filtration
  10. washwashed with diethyl ether, and air
  11. customdried

Sources & evidence

ORD record
ord-f84ba9f8e5be4beca7f52a1b1da276df
Source dataset
uspto-grants-1987_08
Patent number
US04687775

Reaction notes

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