Ethyl chloroacetate → HCID 67857985, compound

HRID 414591Notes

Reaction equation

HRID 414591 reaction equation
[N:1]1([NH:6][C:7]2[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=2)[CH:5]=[CH:4][CH:3]=[CH:2]1.[H-].[Na+].[Cl:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18]>CN(C)C=O>[ClH:15].[CH2:20]([O:19][C:17](=[O:18])[CH2:16][N:6]([C:7]1[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=1)[N:1]1[CH:2]=[CH:3][CH:4]=[CH:5]1)[CH3:21]

Participants

5

Reactant 3

HCID 7751Ethyl chloroacetateHCID 24758Sodium hydrideHCID 10797035HCID 10797035, compound

Product 1

HCID 67857985HCID 67857985, compoundYield 46.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

A solution of N-(1H-pyrrol-1-yl)-4-pyridinamine (5 g) in 25 ml of dimethylformamide was slowly added to a suspension of sodium hydride (60% oil dispersion, 1.4 g, washed with hexane) in 5 ml of dimethylformamide. After the anion formation, the mixture was cooled with an ice-salt bath, and a solution of ethyl chloroacetate (4.2 g) in 5 ml of dimethylformamide was slowly added. After thirty minutes, the mixture was stirred with ice water and extracted with dichloromethane. The organic extract was washed with water and saturated sodium chloride solution, dried over anhydrous magnesium sulfate, filtered and evaporated to 8 g of oil. This oil was purified by HPLC (silica, ethyl acetate) to give 4.1 g of solid, mp 92°-95°. This material was converted to the hydrochloride salt and recrystallized twice from isopropanol and once from ethanol to give 2.6 g of crystals, d 240°-241°.

Workup

  1. temperatureAfter the anion formation, the mixture was cooled with an ice-salt bath
  2. waitAfter thirty minutes
  3. extractionextracted with dichloromethane
  4. extractionThe organic extract
  5. washwas washed with water and saturated sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customevaporated to 8 g of oil
  9. customThis oil was purified by HPLC (silica, ethyl acetate)

Sources & evidence

ORD record
ord-bcbc5904dc024b64aa5872afe8e43d6c
Source dataset
uspto-grants-1988_12
Patent number
US04792562

Reaction notes

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