Sodium hydride → HCID 54347404, compound

HRID 2394486Notes

Reaction equation

HRID 2394486 reaction equation
[C:1]([NH:4][N:5]=[CH:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:9][CH:8]=1)(=[O:3])[CH3:2].[H-].[Na+].Br[CH2:24][CH2:25][C:26]([O:28][CH3:29])=[O:27]>CN(C=O)C>[C:1]([N:4]([CH2:24][CH2:25][C:26]([O:28][CH3:29])=[O:27])[N:5]=[CH:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:9][CH:8]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 76934Methyl 3-bromopropanoateHCID 4999103HCID 4999103, compound

Product 1

HCID 54347404HCID 54347404, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
80 °C

Procedure

A solution of 5×10-3 moles of 4-(benzyloxy)benzaldehyde acetylhydrazone (1.34 g) in 5 ml of anhydrous DMF is added to 5×10-3 moles of sodium hydride (0.12 g) in suspension in 10 ml of anhydrous DMF. The reaction mixture is heated slowly on a water bath at 80° C. for 30 minutes. After cooling, a solution containing 0.85 g (5.1×10-3 moles) of methyl 3-bromopropionate in 5 ml of DMF is slowly added to the mixture. The latter is stirred for one hour at room temperature, then it is poured into 100 ml of ice-cold water. A product precipitates. After standing for 30 minutes, it is filtered, subjected to draining, at the end of which it is chromatographed on a MACHEREY-NAGEL silica gel 60 (0.04-0.063 ml) using a mixture of ethyl acetate and dichloromethane (1/9) as eluent. The oil obtained precipitates. The compound (I-a5) is slowly recrystallized from ether. Its melting point is 170° C. The reaction yield is 11%.

Workup

  1. temperatureAfter cooling
  2. additionis slowly added to the mixture
  3. customA product precipitates
  4. waitAfter standing for 30 minutes
  5. filtrationit is filtered
  6. customis chromatographed on a MACHEREY-NAGEL silica gel 60 (0.04-0.063 ml)
  7. additiona mixture of ethyl acetate and dichloromethane (1/9) as eluent
  8. customThe oil obtained
  9. customprecipitates
  10. customThe compound (I-a5) is slowly recrystallized from ether
  11. customThe reaction yield is 11%

Sources & evidence

ORD record
ord-918681ab388348f09f4df2b6c0d8a69f
Source dataset
uspto-grants-1998_09
Patent number
US05811456

Reaction notes

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