Hydrochloric Acid → HCID 23037408, compound

HRID 623066Notes

Reaction equation

HRID 623066 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:16]([CH2:17][C:18]([NH:20][CH2:21][CH2:22][N:23]([CH2:26][CH3:27])[CH2:24][CH3:25])=[O:19])[C:11]3=[N:12][CH:13]=[CH:14][CH:15]=[C:10]3[N:9]=2)=[CH:4][CH:3]=1.Cl>C(O)(C)C>[OH2:19].[ClH:1].[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:16]([CH2:17][C:18]([NH:20][CH2:21][CH2:22][N:23]([CH2:26][CH3:27])[CH2:24][CH3:25])=[O:19])[C:11]3=[N:12][CH:13]=[CH:14][CH:15]=[C:10]3[N:9]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 14390350HCID 14390350, compound

Product 1

HCID 23037408HCID 23037408, compoundYield 178.4%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of crude 2-(4-chlorophenyl)-N-[2-(diethylamino)ethyl]-3H-imidazo[4,5-b]-pyridine-3-acetamide (3.21 g, 0.0112 mole) in hot isopropyl alcohol was treated with ethereal hydrogen chloride until acidic. The solution was evaporated to dryness, the residue dissolved in hot isopropyl alcohol and the solution was filtered while hot. Solid precipitated upon cooling to room temperature. Isopropyl ether was added and the solid was collected by filtration and rinsed with isopropyl ether. The solid was dried under high vacuum to give 4.4 g (84%) of title compound, mp. 193°-196° C.

Workup

  1. customThe solution was evaporated to dryness
  2. dissolutionthe residue dissolved in hot isopropyl alcohol
  3. filtrationthe solution was filtered while hot
  4. customSolid precipitated
  5. additionIsopropyl ether was added
  6. filtrationthe solid was collected by filtration
  7. washrinsed with isopropyl ether
  8. customThe solid was dried under high vacuum

Sources & evidence

ORD record
ord-7a01c64c122143b4a576c28321fcdc36
Source dataset
uspto-grants-1988_09
Patent number
US04772600

Reaction notes

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