Phenylacetyl chloride → HCID 19774552, compound

HRID 414590Notes

Reaction equation

HRID 414590 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.C(=O)(O)[O-].[Na+].[C:18]1([CH2:24][C:25]([Cl:27])=[O:26])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>ClCCl>[ClH:27].[N:10]1[CH:11]=[CH:12][C:7]([N:6]([N:1]2[CH:2]=[CH:3][CH:4]=[CH:5]2)[C:25](=[O:26])[CH2:24][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 7679Phenylacetyl chlorideHCID 516892Sodium BicarbonateHCID 10797035HCID 10797035, compound

Product 1

HCID 19774552HCID 19774552, compoundYield 84.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of N-(1H-pyrrol-1-yl)-4-pyridinamine (6 g) in 400 ml of dichloromethane containing sodium bicarbonate (6.3 g) was added a solution of phenylacetyl chloride (6.7 g) in 50 ml of dichloromethane. After stirring four hours at ambient temperature, the reaction mixture was evaporated, stirred with water and extracted with ether. The organic extract was washed with water and saturated sodium chloride solution, dried over anhydrous magnesium sulfate, filtered and evaporated to 11 g of an oil. This oil was purified by flash chromatography (silica, 25% ethyl acetate in dichloromethane) to give 10 g of an oil. This oil was converted to the hydrochloride salt in ethanol to give 10.4 g of crystals, d 203°-205°. A 3 g sample was recrystallized from ethanol-ether to give 2.8 g of needles, d 203°-204°.

Workup

  1. customthe reaction mixture was evaporated
  2. stirringstirred with water
  3. extractionextracted with ether
  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 11 g of an oil
  9. customThis oil was purified by flash chromatography (silica, 25% ethyl acetate in dichloromethane)

Sources & evidence

ORD record
ord-9b59a1f4ba1945df8de5984c086dc818
Source dataset
uspto-grants-1988_12
Patent number
US04792562

Reaction notes

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