Chlorosuccinimide → HCID 14232132, compound

HRID 414593Notes

Reaction equation

HRID 414593 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[N:5]([C:11]1[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=1)[N:6]1[CH:10]=[CH:9][CH:8]=[CH:7]1)[CH3:2].[Cl:18]N1C(=O)CCC1=O.S(=O)(O)[O-].[Na+]>O1CCCC1>[ClH:18].[CH2:1]([O:3][C:4](=[O:17])[N:5]([N:6]1[CH:10]=[CH:9][CH:8]=[C:7]1[Cl:18])[C:11]1[CH:12]=[CH:13][N:14]=[CH:15][CH:16]=1)[CH3:2]

Participants

5

Reactant 3

HCID 31398ChlorosuccinimideHCID 14232111HCID 14232111, compoundHCID 23665763Sodium Bisulfite

Product 1

HCID 14232132HCID 14232132, compoundYield 64.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of N-(4-pyridinyl)-N-(1H-pyrrol-1-yl)carbamic acid ethyl ester (9 g) in 100 ml of anhydrous tetrahydrofuran warmed to 50° was slowly dropped a solution of N-chlorosuccinimide (5.2 g) in 75 ml of anhydrous tetrahydrofuran. After stirring seven hours at 50°, the reaction mixture was cooled, stirred with an aqueous solution of sodium bisulfite and extracted with ethyl acetate. The organic extract was washed with water and saturated sodium chloride and thereafter dried over anhydrous magnesium sulfate, filtered and evaporated to 11.5 g of an oil. This oil was purified by HPLC (silica, 20% ethyl acetate in dichloromethane) to give 3.8 g of the desired product as a solid. This material was converted to the hydrochloride salt and twice recrystallized from isopropanol-ether to give 3.3 g of crystals, d 139°-140° C.

Workup

  1. temperaturethe reaction mixture was cooled
  2. extractionextracted with ethyl acetate
  3. extractionThe organic extract
  4. washwas washed with water and saturated sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated to 11.5 g of an oil
  8. customThis oil was purified by HPLC (silica, 20% ethyl acetate in dichloromethane)

Sources & evidence

ORD record
ord-380956924e874b3c84c0d90a0ee60926
Source dataset
uspto-grants-1988_12
Patent number
US04792562

Reaction notes

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