1,3-Propanediol → HCID 22004368, compound

HRID 324352Notes

Reaction equation

HRID 324352 reaction equation
[H-].[Na+].[CH2:3]([OH:7])[CH2:4][CH2:5][OH:6].[Cl:8][C:9]1[CH:10]=[C:11]([CH:26]=[CH:27][C:28]=1[O:29][CH3:30])[CH2:12][NH:13][C:14]1[C:23]2[C:18](=[CH:19][CH:20]=[C:21]([Cl:24])[CH:22]=2)[C:17](Cl)=[N:16][N:15]=1>O>[Cl:24][C:21]1[CH:22]=[C:23]2[C:18](=[CH:19][CH:20]=1)[C:17]([O:6][CH2:5][CH2:4][CH2:3][OH:7])=[N:16][N:15]=[C:14]2[NH:13][CH2:12][C:11]1[CH:26]=[CH:27][C:28]([O:29][CH3:30])=[C:9]([Cl:8])[CH:10]=1

Participants

5

Reactant 3

HCID 104421,3-PropanediolHCID 24758Sodium hydrideHCID 10761565HCID 10761565, compound

Product 1

HCID 22004368HCID 22004368, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

60% Sodium hydride (0.12 g, 3.0 mmol) was added to 8 ml of 1,3-propanediol. The obtained mixture was stirred at room temperature for one hour, followed by the addition of 1.0 g (2.7 mmol) of the compound prepared in Example 27. The obtained mixture was stirred at 150° C. for one hour, followed by the addition of water. The resulting mixture was extracted with ethyl acetate. The organic phase was washed with water and a saturated aqueous solution of common salt, dried over anhydrous magnesium sulfate and freed from the solvent by distillation. The residue was purified by silica gel column chromatography [solvent: dichloromethane/methanol (30:1)] and recrystallized from aqueous ethanol to give 0.58 g of the title compound as white needles.

Workup

  1. stirringThe obtained mixture was stirred at 150° C. for one hour
  2. extractionThe resulting mixture was extracted with ethyl acetate
  3. washThe organic phase was washed with water
  4. dry with materiala saturated aqueous solution of common salt, dried over anhydrous magnesium sulfate
  5. distillationfreed from the solvent by distillation
  6. customThe residue was purified by silica gel column chromatography [solvent: dichloromethane/methanol (30:1)]
  7. customrecrystallized from aqueous ethanol

Sources & evidence

ORD record
ord-a228a3f0e51943c0a1807f8e7d0ea96a
Source dataset
uspto-grants-2001_04
Patent number
US06218392B1

Reaction notes

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