HCID 14232131, compound → HCID 14232124, compound

HRID 1199397Notes

Reaction equation

HRID 1199397 reaction equation
C(OC(=O)[N:5]([N:12]1[CH:16]=[CH:15][CH:14]=[C:13]1[Cl:17])[C:6]1[CH:11]=[CH:10][N:9]=[CH:8][CH:7]=1)C>C(O)C.[OH-].[Na+].O>[ClH:17].[Cl:17][C:13]1[N:12]([NH:5][C:6]2[CH:11]=[CH:10][N:9]=[CH:8][CH:7]=2)[CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 1

HCID 14232131HCID 14232131, compound

Product 1

HCID 14232124HCID 14232124, compoundYield 134.7%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

A mixture prepared from a solution of N-(2-chloro-1H-pyrrol-1-yl)-N-(4-pyridinyl)carbamic acid ethyl ester (6 g) in 50 ml of ethanol and 20 ml of 10% aqueous sodium hydroxide solution was warmed for 15 minutes on a steam bath, and thereafter cooled, diluted with 500 ml of water and extracted with dichloromethane. The organic extract was washed with water and saturated sodium chloride and thereafter dried over anhydrous magnesium sulfate, filtered and evaporated to 5 g of an oil. This oil was purified by HPLC (silica, ethyl acetate) to give 3.5 g of a solid, mp 115°-118° C. This material was converted to the hydrochloride salt and recrystallized twice from isopropanol-ether to give 3.4 g of crystals, mp 172°-173° C.

Workup

  1. temperaturewas warmed for 15 minutes on a steam bath
  2. temperaturecooled
  3. extractionextracted with dichloromethane
  4. extractionThe organic extract
  5. washwas washed with water and saturated sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customevaporated to 5 g of an oil
  9. customThis oil was purified by HPLC (silica, ethyl acetate)

Sources & evidence

ORD record
ord-1284b8942ff347e7b7d492da30801de5
Source dataset
uspto-grants-1990_02
Patent number
US04900742

Reaction notes

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