Sodium Hydroxide → HCID 86757621, compound

HRID 2267998Notes

Reaction equation

HRID 2267998 reaction equation
C([Li])CCC.Br[C:7]1[CH:8]=[N:9][N:10]([CH2:13][CH3:14])[C:11]=1[Cl:12].[CH3:15][C:16]1([CH3:32])[C:25]2[C:20](=[C:21]([CH3:29])[C:22]([C:26](Cl)=O)=[CH:23][CH:24]=2)[S:19](=[O:31])(=[O:30])[CH2:18][CH2:17]1.[OH-:33].[Na+]>CCCCCC.C(OCC)C.CO>[Cl:12][C:11]1[N:10]([CH2:13][CH3:14])[NH:9][C:8](=[C:7]=[O:33])[C:26]=1[C:22]1[C:21]([CH3:29])=[C:20]2[C:25]([C:16]([CH3:32])([CH3:15])[CH2:17][CH2:18][S:19]2(=[O:31])=[O:30])=[CH:24][CH:23]=1

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 11011614HCID 11011614, compoundHCID 11106614HCID 11106614, compoundHCID 178418339Butyllithium

Product 1

HCID 86757621HCID 86757621, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent2×HCID 8058HexaneSolvent

Procedure

Under an atmosphere of protective gas and at 20 to 25° C., 2.6 ml (4.11 mmol) of n-butyllithium in hexane (1.6 molar) were rapidly added dropwise to 0.86 g (4.11 mmol) of 4-bromo-5-chloro-1-ethylpyrazole in 30 ml of diethyl ether. The mixture was stirred at room temperature for 15 minutes and the resulting suspension was then, at −70° C., added dropwise to a solution of 2.2 g (8.21 mmol) of 4,4,8-trimethyl-1,1-dioxothiochroman-7-carbonyl chloride in 30 ml of diethyl ether. The reaction mixture was subsequently warmed to room temperature and mixed with 11 ml of methanol and 26 ml of 2N aqueous sodium hydroxide solution. The organic phase was then separated off, dried and concentrated and the residue was chromatographed over silica gel (mobile phase: ethyl acetate/cyclohexane=3/2).

Workup

  1. temperatureThe reaction mixture was subsequently warmed to room temperature
  2. customThe organic phase was then separated off
  3. customdried
  4. concentrationconcentrated
  5. customthe residue was chromatographed over silica gel (mobile phase: ethyl acetate/cyclohexane=3/2)

Sources & evidence

ORD record
ord-63015decbfb2496385e2f957678d59ae
Source dataset
uspto-grants-2001_12
Patent number
US06326333B1

Reaction notes

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