Hydrochloric Acid → HCID 20085609, compound

HRID 1608815Notes

Reaction equation

HRID 1608815 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10](Cl)(=[O:12])=[O:11])([O-:3])=[O:2].[NH2:14][CH2:15][CH2:16][C:17]1[NH:18][CH:19]=[CH:20][N:21]=1.Cl>ClCCl.N1C=CC=CC=1.O.CO>[NH:18]1[CH:19]=[CH:20][N:21]=[C:17]1[CH2:16][CH2:15][NH:14][S:10]([C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2])(=[O:12])=[O:11]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 155402-Nitrobenzenesulfonyl chlorideHCID 3082145Isohistamine

Product 1

HCID 20085609HCID 20085609, compoundYield 53.9%

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 6344DichloromethaneSolventHCID 22242641Methanol--water (1/1)Solvent

Procedure

A solution of 105 g (0.472 mol) of o-nitrobenzenesulfonyl chloride in 100 ml of dichloromethane was added slowly to a cold (0° C.) solution of 26.2 g (0.236 mol) of 2-(2-aminoethyl)imidazole in 300 ml of pyridine, under nitrogen. The reaction mixture was gradually warmed to room temperature and allowed to react overnight. When the reaction was complete, as determined by thin layer chromatography, the solution was reduced to dryness under reduced pressure. The resultant residue was dissolved in a water/methanol/5N sodium hydroxide solution and stirred for 3 hours. The solution was then acidified with concentrated hydrochloric acid and filtered to remove inorganic impurities. The methanol was removed under reduced pressure from the reaction mixture and the remaining solution was basicified by addition of aqueous sodium bicarbonate. The desired product was extracted from this solution with a solution consisting of ethyl acetate and a small amount of ethanol. The organic extract was washed with water, dried with anhydrous sodium sulfate and reduced to dryness under reduced pressure to provide an oil. This oil was then purified using standard purification techniques to provide 37.7 g of the desired subtitled intermediate.

Workup

  1. customto react overnight
  2. filtrationfiltered
  3. customto remove inorganic impurities
  4. customThe methanol was removed under reduced pressure from the reaction mixture
  5. additionthe remaining solution was basicified by addition of aqueous sodium bicarbonate
  6. extractionThe desired product was extracted from this solution with a solution
  7. extractionThe organic extract
  8. washwas washed with water
  9. dry with materialdried with anhydrous sodium sulfate
  10. customto provide an oil
  11. customThis oil was then purified
  12. custompurification techniques

Sources & evidence

ORD record
ord-aecf409100f54c00acd0a613e4007300
Source dataset
uspto-grants-1995_03
Patent number
US05397798

Reaction notes

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