Sodium Carbonate → HCID 86707692, compound

HRID 570108Notes

Reaction equation

HRID 570108 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[C:9]1[C:10](=[O:23])[N:11]([CH3:22])[C:12]2([CH2:19][CH2:18][N:17]([O:20][CH3:21])[CH2:16][CH2:15]2)[C:13]=1[OH:14].C(=O)([O-])O.[Na+].S(Cl)([Cl:32])(=O)=O.C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)(Cl)Cl>[Cl:32][C:9]1([C:3]2[CH:4]=[C:5]([CH3:8])[CH:6]=[CH:7][C:2]=2[CH3:1])[C:13](=[O:14])[C:12]2([CH2:19][CH2:18][N:17]([O:20][CH3:21])[CH2:16][CH2:15]2)[N:11]([CH3:22])[C:10]1=[O:23]

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 24648Sulfuryl chlorideHCID 516892Sodium BicarbonateHCID 58537984HCID 58537984, compound

Product 1

HCID 86707692HCID 86707692, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 3-(2,5-dimethyl-phenyl)-4-hydroxy-8-methoxy-1-methyl-1,8-diaza-spiro[4.5]dec-3-en-2-one (compound P2.1) (35 mg, 0.111 mmol) and sodium hydrogen carbonate (23 mg, 0.274 mmol) in chloroform (5 ml) at −5° C. was added sulfuryl chloride (0.009 ml, 15.0 mg, 0.111 mmol) in chloroform (0.25 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 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: 26 mg of 3-chloro-3-(2,5-dimethyl-phenyl)-8-methoxy-1-methyl-1,8-diaza-spiro[4.5]decane-2,4-dione (title compound P1.5) as a pale yellow gum.

Workup

  1. customthe layers 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-f412eba9c4ba46ee904c80c3d3620814
Source dataset
uspto-grants-2015_05
Patent number
US09023760B2

Reaction notes

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