Water → N-(2,6-diisopropylphenyl)-2-(2,4-dioxo-1-phenyl-1,3-diazaspiro[4.4]non-3-yl)acetamide

HRID 1666723

Reaction equation

HRID 1666723 reaction equation
C(=O)([O-])[O-].[K+].[K+].[C:7]1([N:13]2[C:17]3([CH2:21][CH2:20][CH2:19][CH2:18]3)[C:16](=[O:22])[NH:15][C:14]2=[O:23])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.Cl[CH2:25][C:26]([NH:28][C:29]1[C:34]([CH:35]([CH3:37])[CH3:36])=[CH:33][CH:32]=[CH:31][C:30]=1[CH:38]([CH3:40])[CH3:39])=[O:27].O>CN(C)C=O>[CH:38]([C:30]1[CH:31]=[CH:32][CH:33]=[C:34]([CH:35]([CH3:36])[CH3:37])[C:29]=1[NH:28][C:26](=[O:27])[CH2:25][N:15]1[C:16](=[O:22])[C:17]2([CH2:21][CH2:20][CH2:19][CH2:18]2)[N:13]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:14]1=[O:23])([CH3:39])[CH3:40]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 23637742-Chloro-N-(2,6-diisopropylphenyl)acetamideHCID 674464041-Phenyl-1,3-diazaspiro[4.4]nonane-2,4-dione

Product 1

HCID 25226594N-(2,6-diisopropylphenyl)-2-(2,4-dioxo-1-phenyl-1,3-diazaspiro[4.4]non-3-yl)acetamideYield 51.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

80 mg (0.57 mmol) of potassium carbonate are added to a solution of 120 mg (0.52 mmol) of 1-phenyl-1,3-diazaspiro[4.4]nonane-2,4-dione and 145 mg (0.57 mmol) of 2-chloro-N-(2,6-diisopropylphenyl)acetamide in 20 ml of dimethylformamide. The reaction medium is stirred at room temperature for 24 hours. It is then poured into water and extracted with ethyl acetate. The organic phases are collected, washed with water and dried over sodium sulfate. The solvents are evaporated. The residue is chromatographed on silica gel (heptane and then heptane/ethyl acetate 80/20, v/v). 120 mg of N-(2,6-diisopropylphenyl)-2-(2,4-dioxo-1-phenyl-1,3-diazaspiro[4.4]non-3-yl)acetamide are obtained in the form of a white solid. Yield=51%, m.p.=275-7° C.

Workup

  1. extractionextracted with ethyl acetate
  2. customThe organic phases are collected
  3. washwashed with water
  4. dry with materialdried over sodium sulfate
  5. customThe solvents are evaporated
  6. customThe residue is chromatographed on silica gel (heptane

Sources & evidence

ORD record
ord-669f38638c9d4929801802c3f4a7f395
Source dataset
uspto-grants-2011_10
Patent number
US08044082B2

Linked notes

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