Triethylamine → HCID 22595760, compound

HRID 2268783Notes

Reaction equation

HRID 2268783 reaction equation
CS([Cl:5])(=O)=O.[CH3:6][C:7]1([CH3:23])[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([S:17][CH3:18])[CH:14]=2)[N:9]([CH2:19][CH2:20]O)[C:8]1=[O:22].C(N(CC)CC)C>ClCCl>[Cl:5][CH2:20][CH2:19][N:9]1[C:10]2[C:15](=[CH:14][C:13]([S:17][CH3:18])=[CH:12][CH:11]=2)[CH2:16][C:7]([CH3:23])([CH3:6])[C:8]1=[O:22]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 18332430HCID 18332430, compound

Product 1

HCID 22595760HCID 22595760, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methanesulfonyl chloride (1.05 ml, 1.56 g, 0.014 mol) was added to a solution of 3,4-dihydro-3,3-dimethyl-1-(2-hydroxyethyl)-6-methylthio-2(1H)-quinolinone (2.88 g, 0.011 mol) and triethylamine (2.27 ml, 1.64 g, 0.016 mol) in dichloromethane (50 ml) at 0° C. under nitrogen and the resultant mixture was stirred for 20 mins. Then the mixture was allowed to warm to room temperature and sirred for 20 hr. The reaction mixture was then washed with water (2×20 ml), dried (MgSO4), filtered and concentrated in vacuo. The residue was then dissolved in carbon tetrachloride (30 ml), filtered and the solvent was evaporated in vacuo to afford 1-(2-chloroethyl)-3,3-dimethyl-6-methylthio-2(1H)-quinolinone as an oil which solidified on standing.

Workup

  1. washThe reaction mixture was then washed with water (2×20 ml)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. dissolutionThe residue was then dissolved in carbon tetrachloride (30 ml)
  6. filtrationfiltered
  7. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-9d5b6ad9b58346bf9cefa802b9f3a57a
Source dataset
uspto-grants-2001_12
Patent number
US06329366B1

Reaction notes

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