Pyridine → HCID 54735801, compound

HRID 2293687Notes

Reaction equation

HRID 2293687 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.N1C=CC=CC=1.Cl[CH2:30][CH2:31][S:32](Cl)(=[O:34])=[O:33]>C(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:32]([CH:31]=[CH2:30])(=[O:34])=[O:33])[CH:7]=[CH:6][CH:5]=1)[CH2:9][CH3:10]

Participants

5

Reactant 3

HCID 1049PyridineHCID 15385Ethanesulfonylchloride, 2-chloro-HCID 54713033HCID 54713033, compound

Product 1

HCID 54735801HCID 54735801, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To 14.7 mg of 3-[1-(3-aminophenyl)propyl]4 hydroxy-coumarin is added 1 ml of methylene chloride and 8.1 microliters of pyridine. 5.71 microliters of chloroethylsulfonyl chloride is added at room temperature and protection from moisture. The reaction mixture is allowed to stir at room temperature for 3 hours. 5 ml of methylene chloride is added and the solution is washed twice with 5 ml of water. The organic solution is dried over anhydrous sodium sulfate, filtered and dried to give crude title product. Chromatography over 15 g of silica gel using 5% methanol in chloroform and collecting material with Rf =0.3 gives 6.3 mg of the title product.

Workup

  1. washthe solution is washed twice with 5 ml of water
  2. dry with materialThe organic solution is dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. customdried
  5. customto give crude title product
  6. customChromatography over 15 g of silica gel using 5% methanol in chloroform and collecting material with Rf =0.3

Sources & evidence

ORD record
ord-8fb7d4d125944a0c8b739f2fc4acb102
Source dataset
uspto-grants-1997_11
Patent number
US05686486

Reaction notes

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