Hydrochloric Acid → HCID 18977188, compound

HRID 2393744Notes

Reaction equation

HRID 2393744 reaction equation
Br.[NH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:14]=[CH:15][C:16](=[O:19])[NH:17][N:18]=2)=[CH:9][CH:8]=1.CN(C)C1C=CC=CC=1.C[Si](C)(C)Cl.Cl[CH2:35][CH2:36][S:37](Cl)(=[O:39])=[O:38].Cl>ClCCl.C(N(CC)CC)C>[CH:36]([S:37]([NH:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]2[CH:14]=[CH:15][C:16](=[O:19])[NH:17][N:18]=2)=[CH:11][CH:12]=1)(=[O:39])=[O:38])=[CH2:35]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 949N,N-DimethylanilineHCID 6397ChlorotrimethylsilaneHCID 15385Ethanesulfonylchloride, 2-chloro-HCID 18977159HCID 18977159, compound

Product 1

HCID 18977188HCID 18977188, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

276 mg of triethylamine was added to a dichloromethane suspension (4 ml) containing 100 mg of 6-[4-(3-aminopropoxy)phenyl]pyridazin-3(2H)-one hydrobromide and 37 mg of dimethylaniline, and the mixture was stirred at room temperature for 30 minutes. Under ice cooling, 86 mg of trimethylchlorosilane was added thereto, and the mixture was stirred at room temperature for 2 hours. Again, under ice cooling, a dichloromethane solution (1 ml) containing 65 mg of chloroethylsulfonyl chloride was added dropwise to the mixture, and the resulting mixture was stirred at room temperature for 30 minutes. 5 ml of 1M hydrochloric acid was added to the mixture, and the organic layer was collected by separation. After the organic layer was washed with water and dried, the solvent was removed. The residue was purified by silica gel column chromatography (eluent: chloroform-methanol (30:1)) to obtain 73 mg of 6-[4-(3-vinylsulfonylaminopropoxy)phenyl]pyridazin-3(2H)-one.

Workup

  1. stirringthe mixture was stirred at room temperature for 2 hours
  2. additionwas added dropwise to the mixture
  3. stirringthe resulting mixture was stirred at room temperature for 30 minutes
  4. customthe organic layer was collected by separation
  5. washAfter the organic layer was washed with water
  6. customdried
  7. customthe solvent was removed
  8. customThe residue was purified by silica gel column chromatography (eluent: chloroform-methanol (30:1))

Sources & evidence

ORD record
ord-0f57f9dbd87e4360aca9767539793bfb
Source dataset
uspto-grants-1998_09
Patent number
US05808065

Reaction notes

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