Sodium Carbonate → HCID 86707690, compound

HRID 570107Notes

Reaction equation

HRID 570107 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([CH3:9])=[CH:4][C:3]=1[CH:10]1[C:14](=[O:15])[C:13]2([CH2:20][CH2:19][N:18]([O:21][CH3:22])[CH2:17][CH2:16]2)[N:12]([CH3:23])[C:11]1=[O:24].C(=O)([O-])O.[Na+].S(Cl)([Cl:33])(=O)=O.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl>[Cl:33][C:10]1([C:3]2[CH:4]=[C:5]([CH3:9])[C:6]([CH3:8])=[CH:7][C:2]=2[Cl:1])[C:14](=[O:15])[C:13]2([CH2:20][CH2:19][N:18]([O:21][CH3:22])[CH2:17][CH2:16]2)[N:12]([CH3:23])[C:11]1=[O:24]

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 24648Sulfuryl chlorideHCID 516892Sodium BicarbonateHCID 86707691HCID 86707691, compound

Product 1

HCID 86707690HCID 86707690, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 3-(2-chloro-4,5-dimethyl-phenyl)-8-methoxy-1-methyl-1,8-diaza-spiro[4.5]decane-2,4-dione (compound P2.26) (120 mg, 0.342 mmol) and sodium hydrogen carbonate (72 mg, 0.857 mmol) in dichloromethane (5 ml) at −5° C. was added sulfuryl chloride (0.026 ml, 43.3 mg, 0.321 mmol) in dichloromethane (0.5 ml) dropwise. The reaction mixture was stirred at 0° C. for 1.5 hour, 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). Yield: 120 mg of 3-chloro-3-(2-chloro-4,5-dimethyl-phenyl)-8-methoxy-1-methyl-1,8-diaza-spiro[4.5]decane-2,4-dione (title compound P1.1) as a white solid, mp 93-94° C.

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)

Sources & evidence

ORD record
ord-b7d72ced91864ba8901d7440e0f14fe2
Source dataset
uspto-grants-2015_05
Patent number
US09023760B2

Reaction notes

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