Sodium Carbonate → HCID 86707695, compound

HRID 570111Notes

Reaction equation

HRID 570111 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=2)[CH:5]=[C:6]([CH3:23])[C:7]=1[C:8]1[C:9](=[O:22])[N:10]([CH3:21])[C:11]2([CH2:18][CH2:17][N:16]([O:19][CH3:20])[CH2:15][CH2:14]2)[C:12]=1[OH:13].C(=O)([O-])O.[Na+].S(Cl)([Cl:39])(=O)=O.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl>[Cl:39][C:8]1([C:7]2[C:6]([CH3:23])=[CH:5][C:4]([C:24]3[CH:25]=[CH:26][C:27]([Cl:30])=[CH:28][CH:29]=3)=[CH:3][C:2]=2[Cl:1])[C:12](=[O:13])[C:11]2([CH2:14][CH2:15][N:16]([O:19][CH3:20])[CH2:17][CH2:18]2)[N:10]([CH3:21])[C:9]1=[O:22]

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 24648Sulfuryl chlorideHCID 516892Sodium BicarbonateHCID 86707694HCID 86707694, compound

Product 1

HCID 86707695HCID 86707695, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 3-(3,4′-dichloro-5-methyl-biphenyl-4-yl)-4-hydroxy-8-methoxy-1-methyl-1,8-diaza-spiro[4.5]dec-3-en-2-one (100 mg, 0.224 mmol) and sodium hydrogen carbonate (47 mg, 0.560 mmol) in dichloromethane (5 ml) at −5° C. was added sulfuryl chloride (0.017 ml, 28.3 mg, 0.210 mmol) in dichloromethane (0.5 ml) dropwise. The reaction mixture was stirred at 0° C. for 30 minutes and at room temperature overnight, poured on saturated aqueous sodium carbonate, the layers were separated, the water phase extracted with ethyl acetate (3×20 ml), the combined organic phases washed with saturated aqueous sodium carbonate and brine, dried over sodium sulfate and concentrated. The residue was purified by chromatography on silica gel (ethyl acetate/cyclohexane 2:1). Yield: 65 mg of 3-chloro-3-(3,4′-dichloro-5-methyl-biphenyl-4-yl)-8-methoxy-1-methyl-1,8-diaza-spiro[4.5]decane-2,4-dione (title compound P1.9) as a gum.

Workup

  1. customthe layers were separated
  2. extractionthe water phase extracted with ethyl acetate (3×20 ml)
  3. washthe combined organic phases washed with saturated aqueous sodium carbonate and brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by chromatography on silica gel (ethyl acetate/cyclohexane 2:1)

Sources & evidence

ORD record
ord-8826149efdf3482794308d4966e6657a
Source dataset
uspto-grants-2015_05
Patent number
US09023760B2

Reaction notes

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