Acetone → HCID 2842843, compound

HRID 1608813Notes

Reaction equation

HRID 1608813 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][CH2:17][N:18]1[CH:22]=[CH:21][N:20]=[CH:19]1.C(O)C.CC(=O)C>ClCCl.N1C=CC=CC=1.C(OCC)(=O)C>[N:18]1([CH2:17][CH2:16][CH2:15][NH:14][S:10]([C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N+:1]([O-:3])=[O:2])(=[O:12])=[O:11])[CH:22]=[CH:21][N:20]=[CH:19]1

Participants

8

Reactant 4

HCID 180AcetoneHCID 702EthanolHCID 155402-Nitrobenzenesulfonyl chlorideHCID 787361H-Imidazole-1-propanamine

Product 1

HCID 2842843HCID 2842843, compoundYield 25.5%

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 11.5 g (0.0519 mol) of o-nitrobenzenesulfonyl chloride in approximately 30 ml of dichloromethane was added slowly over several minutes to a cold (0° C.) solution of 5.4 g (0.043 mol) of N-(3-aminopropyl)imidazole in 100 ml pyridine, under nitrogen. The resulting 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 reaction solution was reduced to dryness under reduced pressure. The resultant oil was redissolved in an ethyl acetate/aqueous sodium bicarbonate mixture containing trace amounts of ethanol and propanone. The resulting layers were separated, the organic layer was washed with water and then reduced to dryness under reduced pressure to provide a gum. This gum was then purified using column chromatography (8000 ml of a gradient eluent of 0-10% methanol in dichloromethane). The fractions containing the desired product were combined, reduced to dryness under reduced pressure and then recrystallized from methanol to provide 3.4 g of the desired subtitled intermediate (m.p. 166°-170° C).

Workup

  1. customThe resulting reaction mixture
  2. customto react overnight
  3. customThe resulting layers were separated
  4. washthe organic layer was washed with water
  5. customto provide a gum
  6. customThis gum was then purified
  7. additionThe fractions containing the desired product
  8. customrecrystallized from methanol

Sources & evidence

ORD record
ord-35f83095c7cb41ce99c01e3ab0d1c389
Source dataset
uspto-grants-1995_03
Patent number
US05397798

Reaction notes

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