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Methanesulfonyl chloride → 8-(2,6-Dichlorobenzoylamino)-4-(2-methanesulfonylhydrazino)quinoline

HRID 613552
Notes
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Reaction equation

HRID 613552 reaction equation
[Cl:1][C:2]1[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[C:3]=1[C:4]([NH:6][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:16]=1[N:15]=[CH:14][CH:13]=[C:12]2[NH:17][NH2:18])=[O:5].[CH3:24][S:25](Cl)(=[O:27])=[O:26]>N1C=CC=CC=1.CN(C)C=O>[Cl:1][C:2]1[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[C:3]=1[C:4]([NH:6][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:16]=1[N:15]=[CH:14][CH:13]=[C:12]2[NH:17][NH:18][S:25]([CH3:24])(=[O:27])=[O:26])=[O:5]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 19592850HCID 19592850, compound

Product 1

HCID 195923418-(2,6-Dichlorobenzoylamino)-4-(2-methanesulfonylhydrazino)quinolineYield 6%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred suspension of 8-(2,6-dichlorobenzoylamino)-4-hydrazinoquinoline (216 mg) in pyridine (2 ml) was added a solution of methanesulfonyl chloride (78.4 mg) in dimethylformamide under ice-cooling, and the mixture was stirred for 50 minutes at the same temperature. The mixture was concentrated in vacuo, and ethyl acetate, methanol and water were added to the residue. The separated organic layer was washed with water and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by preparative thin layer chromatography and recrystallized from ethanol to give 8-(2,6-dichlorobenzoylamino)-4-(2-methanesulfonylhydrazino)quinoline (16 mg).

Workup

  1. temperaturecooling
  2. concentrationThe mixture was concentrated in vacuo, and ethyl acetate, methanol and water
  3. additionwere added to the residue
  4. washThe separated organic layer was washed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was purified by preparative thin layer chromatography
  8. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-f7598097424643589c4043e61ed3bdfb
Source dataset
uspto-grants-1999_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06008230

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes