Chlorosuccinimide → HCID 14232130, compound

HRID 1955657Notes

Reaction equation

HRID 1955657 reaction equation
[CH3:1][N:2]([N:9]1[CH:13]=[CH:12][CH:11]=[CH:10]1)[C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1.[Cl:14]N1C(=O)CCC1=O.S(=O)(O)[O-].[Na+]>O1CCCC1>[ClH:14].[Cl:14][C:10]1[N:9]([N:2]([CH3:1])[C:3]2[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=2)[CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 31398Chlorosuccinimide2×HCID 10559130HCID 10559130, compoundHCID 23665763Sodium Bisulfite

Product 1

HCID 14232130HCID 14232130, compoundYield 92.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-methyl-N-(1H-pyrrol-1-yl)-4-pyridinamine (7.7 g) in 300 ml of anhydrous tetrahydrofuran cooled to 5° C. with an ice bath was added N-chlorosuccinimide (5.2 g). The reaction mixture was stirred sixty hours at ambient temperature, and thereafter additional N-chlorosuccinimide (0.9 g) was added. After stirring an additional sixteen hours at ambient temperature, the reaction mixture was stirred with an aqueous solution of sodium bisulfite and extracted with ether. The organic extract was washed with water and saturated sodium chloride solution and thereafter dried over anhydrous magnesium sulfate, filtered and evaporated to 9.5 g of an oil. This oil was purified by HPLC (silica, ethyl acetate) to give 4.4 g of an oil. This oil was purified by column chromatography (alumina, ether) to give 2.4 g of the desired product as an oil. This oil was dissolved in 25 ml of isopropanol, filtered, and converted to the hydrochloride salt by the addition of ethereal hydrochloric acid. The solution was diluted with 25 ml of ether and cooled. The resultant precipitate was collected and dried to give 2.5 g of crystals, m.p. 230°-231° C.

Workup

  1. stirringAfter stirring an additional sixteen hours at ambient temperature
  2. extractionextracted with ether
  3. extractionThe organic extract
  4. washwas washed with water and saturated sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated to 9.5 g of an oil
  8. customThis oil was purified by HPLC (silica, ethyl acetate)

Sources & evidence

ORD record
ord-e8cc1dadc3454fa48b49c341591ad97c
Source dataset
uspto-grants-1998_07
Patent number
US05776955

Reaction notes

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