1,3-Dimethyl-2-imidazolidinone → HCID 18977152, compound

HRID 2393743Notes

Reaction equation

HRID 2393743 reaction equation
C(N(CC)CC)C.CN1CCN(C)C1=O.Br.[NH2:17][CH2:18][CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2[CH:28]=[CH:29][C:30](=[O:33])[NH:31][N:32]=2)=[CH:23][CH:22]=1.Cl[CH2:35][CH2:36][S:37](Cl)(=[O:39])=[O:38]>O1CCCC1>[CH:36]([S:37]([NH:17][CH2:18][CH2:19][CH2:20][C:21]1[CH:22]=[CH:23][C:24]([C:27]2[CH:28]=[CH:29][C:30](=[O:33])[NH:31][N:32]=2)=[CH:25][CH:26]=1)(=[O:39])=[O:38])=[CH2:35]

Participants

6

Reactant 4

HCID 66611,3-Dimethyl-2-imidazolidinoneHCID 8471TriethylamineHCID 15385Ethanesulfonylchloride, 2-chloro-HCID 18977181HCID 18977181, compound

Product 1

HCID 18977152HCID 18977152, compoundYield 37.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3.54 g of triethylamine was added to a 1,3-dimethyl-2-imidazolidinone suspension (35 ml) containing 3.10 g of 6-[4-(3-aminopropyl)phenyl]pyridazin-3(2H)-one hydrobromide. Then, a tetrahydrofuran solution (15 ml) containing 1.95 g of chloroethylsulfonyl chloride was added to the mixture, and the resulting mixture was stirred at room temperature for 5 hours. The reaction mixture was poured into ice water and extracted with chloroform. After the chloroform layer was washed with water and dried, the solvent was removed. The residue was purified by silica gel column chromatography (eluent: chloroform-methanol (10:1)) to obtain 1.19 g of 6-[4-(3-vinylsulfonylaminopropyl)phenyl]-pyridazin-3(2H)-one.

Workup

  1. additionwas added to the mixture
  2. extractionextracted with chloroform
  3. washAfter the chloroform layer was washed with water
  4. customdried
  5. customthe solvent was removed
  6. customThe residue was purified by silica gel column chromatography (eluent: chloroform-methanol (10:1))

Sources & evidence

ORD record
ord-3abf76746bee4313895927b1cd6f726b
Source dataset
uspto-grants-1998_09
Patent number
US05808065

Reaction notes

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