Ethyl Acetate → HCID 21476295, compound

HRID 2293099Notes

Reaction equation

HRID 2293099 reaction equation
C(OCC)(=O)C.Br.[NH2:8][CH2:9][CH:10]1[CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[C:15]([C:19]3[CH:20]=[CH:21][C:22](=[O:25])[NH:23][N:24]=3)[CH:16]=2)[CH2:11]1.C(=O)([O-])[O-].[Na+].[Na+].[CH2:32]([S:34](Cl)(=[O:36])=[O:35])[CH3:33]>O1CCCC1>[CH2:32]([S:34]([NH:8][CH2:9][CH:10]1[CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[C:15]([C:19]3[CH:20]=[CH:21][C:22](=[O:25])[NH:23][N:24]=3)[CH:16]=2)[CH2:11]1)(=[O:36])=[O:35])[CH3:33]

Participants

6

Reactant 4

HCID 8857Ethyl Acetate2×HCID 10340Sodium CarbonateHCID 11667Ethanesulfonyl chlorideHCID 214762912-aminomethyl-5-[pyridazin-3(2H)-on-6-yl]indane hydrobromide

Product 1

HCID 21476295HCID 21476295, compoundYield 82.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In a mixed solution of 30 ml of ethyl acetate and 30 ml of tetrahydrofuran was suspended 3.22 g of 2-aminomethyl-5-[pyridazin-3(2H)-on-6-yl]indane hydrobromide. A sodium carbonate aqueous solution (5.30 g/30 ml of water) was added to the suspension. Under ice cooling, 3.32 g of ethanesulfonyl chloride dissolved in 10 ml of tetrahydrofuran was added to the mixture, and the resulting mixture was stirred for 3 hours. 300 ml of ethyl acetate was added to the mixture. After the organic layer was collected by separation, washed with water and dried, and the solvent was removed. The residue was purified by silica gel column chromatography (chloroform-methanol (100:3)) to obtain 2.75 g of 2-(ethylsulfonylaminomethyl)-5-[pyridazin-3(2H)-on-6-yl]indane.

Workup

  1. additionwas added to the mixture
  2. customAfter the organic layer was collected by separation
  3. washwashed with water
  4. customdried
  5. customthe solvent was removed
  6. customThe residue was purified by silica gel column chromatography (chloroform-methanol (100:3))

Sources & evidence

ORD record
ord-3c61e454e9b64a54b7055d90cbe2b4f2
Source dataset
uspto-grants-1997_11
Patent number
US05686452

Reaction notes

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