Triethylamine → HCID 86743145, compound

HRID 1461820Notes

Reaction equation

HRID 1461820 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([C:12](=[O:21])[C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=1[Cl:20])[CH2:7][CH2:6][C:5]2=[N:22][OH:23].C(N(CC)CC)C.[CH3:31][S:32](Cl)(=[O:34])=[O:33]>ClCCl>[S:32]([OH:34])(=[O:21])(=[O:33])[CH3:31].[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([C:12](=[O:21])[C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=1[Cl:20])[CH2:7][CH2:6][C:5]2=[N:22][OH:23]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 86743146HCID 86743146, compound

Product 1

HCID 86743145HCID 86743145, compoundYield 174.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of 6-chloro-1-(2,4-dichlorobenzo-yl)-2,3-dihydro-4(1H)-quinolinone-4-oxime (10.0 g), triethylamine (4.1 g) and dichloromethane (150 ml) was added dropwise methanesulfonyl chloride (3.5 g) at -20° C. with stirring. The mixture was stirred at -20° C. for 30 minutes and dichloromethane (300 ml) was added. The reaction mixture was sequentially washed with 1 N HCl, saturated aqueous sodium bicarbonate solution, then with saturated aqueous NaCl solution and dried over anhydrous sodium sulfate. Solvent was removed in vacuo and the residue was recrystallized with ether and n-hexane to obtain 6-chloro-1-(2,4-dichlorobenzoyl)-2,3-dihydro-4(1H)-quinolinone-4-oxime mesylate (yield 11 g) as white crystal.

Workup

  1. stirringThe mixture was stirred at -20° C. for 30 minutes
  2. washThe reaction mixture was sequentially washed with 1 N HCl, saturated aqueous sodium bicarbonate solution
  3. dry with materialwith saturated aqueous NaCl solution and dried over anhydrous sodium sulfate
  4. customSolvent was removed in vacuo
  5. customthe residue was recrystallized with ether and n-hexane

Sources & evidence

ORD record
ord-6e8782a57b8143b3a2c192f49222a7e0
Source dataset
uspto-grants-1991_12
Patent number
US05077410

Reaction notes

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