Chloroacetamide → 2-(4-Chlorophenyl)-1H-imidazo[4,5-b]pyridine-1-acetamide

HRID 622008

Reaction equation

HRID 622008 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[NH:18][C:13]3=[N:14][CH:15]=[CH:16][CH:17]=[C:12]3[N:11]=2)=[CH:6][CH:5]=1.Cl[CH2:20][C:21]([NH2:23])=[O:22]>O>[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:11]([CH2:20][C:21]([NH2:23])=[O:22])[C:12]3[C:13]([N:18]=2)=[N:14][CH:15]=[CH:16][CH:17]=3)=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 6580ChloroacetamideHCID 24758Sodium hydrideHCID 178477971HCID 178477971, compound

Product 1

HCID 143904392-(4-Chlorophenyl)-1H-imidazo[4,5-b]pyridine-1-acetamideYield 86%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Under nitrogen flow, sodium hydride (0.96 g, 0.0234 mole, 60% in oil) was washed with hexanes (~70 ml) and decanted. Dimethylformamide was added (100 ml) and the 2-(4-chlorophenyl)-3H-imidazo[4,5-b]pyridine (5.0 g, 0.022 mole) was added in portions. The reaction mixture was heated at 70°-85° C. for 11/2 hours. Chloroacetamide (2.06 g, 0.022 mole) was added and the reaction mixture was stirred overnight at room temperature. The reaction mixture was added to water (~600 ml) and the precipitate was collected by filtration, washed with water, and dried under high vacuum overnight at 50° C. NMR indicated at 14% yield of the isomer: 2-(4-chlorophenyl)-3H-imidazo[4,5-b]pyridine-3-acetamide and an 86% yield of the title compound. The solid was dissolved in pyridine, filtered, and diluted with water to produce crystalline product with refrigeration. The solid was collected by filtration, washed with water and dried under high vacuum at 90° C. overnight to give 2.3 g (36.5%) of the title compound, mp 280°-283° C. with decomposition.

Workup

  1. customdecanted
  2. additionDimethylformamide was added (100 ml)
  3. temperatureThe reaction mixture was heated at 70°-85° C. for 11/2 hours
  4. filtrationthe precipitate was collected by filtration
  5. washwashed with water
  6. customdried under high vacuum overnight at 50° C

Sources & evidence

ORD record
ord-0214e73751824602ae705a0dde000553
Source dataset
uspto-grants-1989_04
Patent number
US04824951

Linked notes

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