Sodium Sulfite → N-(2-Chloro-1H-pyrrol-1-yl)-N-ethyl-4-pyridinamine hydrochloride

HRID 1086885Notes

Reaction equation

HRID 1086885 reaction equation
[CH2:1]([N:3]([N:10]1[CH:14]=[CH:13][CH:12]=[CH:11]1)[C:4]1[CH:9]=[CH:8][N:7]=[CH:6][CH:5]=1)[CH3:2].[Cl:15]N1C(=O)CCC1=O.S([O-])([O-])=O.[Na+].[Na+]>O1CCCC1>[ClH:15].[Cl:15][C:11]1[N:10]([N:3]([CH2:1][CH3:2])[C:4]2[CH:5]=[CH:6][N:7]=[CH:8][CH:9]=2)[CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 24437Sodium SulfiteHCID 31398ChlorosuccinimideHCID 10845273N-ethyl-N-(1H-pyrrol-1-yl)-4-pyridinamine

Product 1

HCID 14232133N-(2-Chloro-1H-pyrrol-1-yl)-N-ethyl-4-pyridinamine hydrochlorideYield 52.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-ethyl-N-(1H-pyrrol-1-yl)-4-pyridinamine (10.2 g) in 200 ml of anhydrous tetrahydrofuran was added N-chlorosuccinimide (7.3 g). After stirring twenty hours at ambient temperature, the reaction mixture was stirred with an aqueous solution of sodium sulfite 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 12 g of an oil. This oil was purified by HPLC (silica, 25% dichloromethane in ethyl acetate) to give 3.7 g of the desired product as an oil. This oil was converted to the hydrochloride salt and twice recrystallized from isopropanol-ether to give 3.1 g of crystals, mp 206°-207° C.

Workup

  1. extractionextracted with dichloromethane
  2. extractionThe organic extract
  3. washwas washed with water and saturated sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customevaporated to 12 g of an oil
  7. customThis oil was purified by HPLC (silica, 25% dichloromethane in ethyl acetate)

Sources & evidence

ORD record
ord-aae96ff7ee7a441cbaf865c69380edc5
Source dataset
uspto-grants-1991_07
Patent number
US05032599

Reaction notes

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