Sodium hydride → HCID 15388570, compound

HRID 612396Notes

Reaction equation

HRID 612396 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[N:6]1[C:10](=[O:11])[C:9]2([CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)[NH:8][C:7]1=[O:17].[H-].[Na+].I[CH2:21][CH2:22][CH3:23]>CN(C)C=O.O>[CH2:21]([N:8]1[C:9]2([CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)[C:10](=[O:11])[N:6]([C:2]2[S:1][CH:5]=[CH:4][N:3]=2)[C:7]1=[O:17])[CH2:22][CH3:23]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 336431-IodopropaneHCID 10220608190734-31-7

Product 1

HCID 15388570HCID 15388570, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

5.05 g of the product from Example 2, stage 2 were dissolved in 20 ml of dimethylformamide. 1.10 g of sodium hydride (50% suspension in mineral oil) were added in portions with stirring at 200C. After 1 hour's stirring, 4 ml of 1-iodopropane were added. Stirring was continued for a further 3 hours. The mixture was then diluted with 100 ml of distilled water, extracted three times with 30 ml portions of ethyl acetate, washed with saturated sodium chloride solution and dried over sodium sulphate. Once the solvent had been removed by distillation, the residue was purified by passage through a silica gel column with ethyl acetate/n-hexane=8/5. 3.95 g of l-propyl-3-thiazol-2-yl-1,3-diazaspiro[4.5]decane-2,4-dione (67% of th.) were obtained in the form of white crystals (mp 135-138° C.).

Workup

  1. stirringStirring
  2. waitwas continued for a further 3 hours
  3. extractionextracted three times with 30 ml portions of ethyl acetate
  4. washwashed with saturated sodium chloride solution
  5. dry with materialdried over sodium sulphate
  6. customOnce the solvent had been removed by distillation
  7. customthe residue was purified by passage through a silica gel column with ethyl acetate/n-hexane=8/5

Sources & evidence

ORD record
ord-34f50492f9254917b0ec8d7921352f4c
Source dataset
uspto-grants-1999_12
Patent number
US06004963

Reaction notes

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