Ethanesulfonyl chloride → HCID 54728442, compound

HRID 2293688Notes

Reaction equation

HRID 2293688 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]([C:11]2[C:12](=[O:22])[O:13][C:14]3[C:19]([C:20]=2[OH:21])=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:9][CH3:10])[CH:5]=[CH:6][CH:7]=1.[CH2:23]([S:25](Cl)(=[O:27])=[O:26])[CH3:24]>C(Cl)Cl.N1C=CC=CC=1.C(Cl)(Cl)Cl>[OH:21][C:20]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[O:13][C:12](=[O:22])[C:11]=1[CH:8]([C:4]1[CH:3]=[C:2]([NH:1][S:25]([CH2:23][CH3:24])(=[O:27])=[O:26])[CH:7]=[CH:6][CH:5]=1)[CH2:9][CH3:10]

Participants

6

Reactant 2

HCID 11667Ethanesulfonyl chlorideHCID 54713033HCID 54713033, compound

Product 1

HCID 54728442HCID 54728442, compound

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent2×

Procedure

14.75 mg of 3-[1-(3-aminophenyl)propyl]-4 hydroxy-coumarin is dissolved in 1 ml of methylene chloride with 8.1 microliters of pyridine added. To this solution, at room temperature with protection from moisture, is added 5.14 microliters of ethylsulfuryl chloride. The reaction is allowed to stir, at room temperature, for 18 hours. 5 ml of methylene chloride is added to the reaction mixture, the resulting mixture is washed twice with 1 ml of water, and the methylene chloride solution is separated, dried over anhydrous sodium sulfate and evaporated to dryness to yield 28 mg of crude title product. Chromatography over 15 g of silica gel using 5% methanol in chloroform as solvent gives 6.8 mg of pure title product.

Workup

  1. additionadded
  2. washthe resulting mixture is washed twice with 1 ml of water
  3. customthe methylene chloride solution is separated
  4. dry with materialdried over anhydrous sodium sulfate
  5. customevaporated to dryness
  6. customto yield 28 mg of crude title product

Sources & evidence

ORD record
ord-49e7de39e61b415684c23369c168154e
Source dataset
uspto-grants-1997_11
Patent number
US05686486

Reaction notes

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