Diethyl Ether → HCID 12897108, compound

HRID 894049Notes

Reaction equation

HRID 894049 reaction equation
[CH:1]1[N:2]=[CH:3][N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12.CCOCC.[Cl:15][C:16]1[CH:25]=[CH:24][C:19]([C:20](=[O:23])[CH2:21][Br:22])=[CH:18][CH:17]=1>O1CCCC1>[Br-:22].[Cl:15][C:16]1[CH:25]=[CH:24][C:19]([C:20]([CH2:21][N+:2]2[CH:1]=[C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][N:4]3[CH:3]=2)=[O:23])=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 68303p-Chlorophenacyl bromideHCID 274090Imidazo(1,5-a)pyridine

Product 1

HCID 12897108HCID 12897108, compoundYield 68.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Imidazo[3,4-a]pyridine (8.3 g., 70 mmoles) dissolved in 125 ml. of ether was mixed with p-chlorophenacyl bromide (16.3 g., 70 mmoles) dissolved in 50 ml. of tetrahydrofuran and stirred at room temperature for 10 minutes at which time a gummy precipitate (approximately 2 g.) was separated by decantation. The decant was stirred for an additional 22 hours at room temperature, by which time product had precipitated heavily. Filtration with ether wash gave 2-(4-chlorobenzoylmethyl)imidazo[3,4-a]pyridinium bromide (16.8 g., m.p. 241°-243° C.).

Workup

  1. dissolutiondissolved in 50 ml
  2. customwas separated by decantation
  3. customhad precipitated heavily
  4. filtrationFiltration with ether
  5. washwash

Sources & evidence

ORD record
ord-b4d6607ca83044178f473dc12a72bef5
Source dataset
uspto-grants-1981_08
Patent number
US04282242

Reaction notes

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