Dimethylformamide → HCID 21250090, compound

HRID 1531680Notes

Reaction equation

HRID 1531680 reaction equation
[H-].[Na+].[CH3:3][O:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][OH:10].CN(C=O)C.N1([C:21]([CH:23]2[C:36](=[O:37])[C:35]3[C:26](=[C:27]4[C:32](=[CH:33][CH:34]=3)[CH:31]=[CH:30][CH:29]=[N:28]4)[N:25]=[CH:24]2)=[O:22])C=CN=C1>C(O)(=O)C>[CH3:3][O:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][O:10][C:21]([CH:23]1[C:36](=[O:37])[C:35]2[C:26](=[C:27]3[C:32](=[CH:33][CH:34]=2)[CH:31]=[CH:30][CH:29]=[N:28]3)[N:25]=[CH:24]1)=[O:22]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8134Diethylene Glycol Monomethyl EtherHCID 24758Sodium hydrideHCID 21250099HCID 21250099, compound

Product 1

HCID 21250090HCID 21250090, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Sodium hydride (3.15 g, 60%) was added in portions to a mixture of 2-(2-methoxyethoxy)ethanol (15 ml) and DMF (200 ml). The mixture was stirred for approximately 30 minutes until effervescence ceased. 3-(Imidazol-1-ylcarbonyl)-4-oxo-3,4-dihydro-1,10-phenanthroline (21.05 g) was added and the mixture stirred for 18 hours. The mixture was acidified to pH 5-6 with acetic acid, and evaporated to dryness under reduced pressure. Water (50 ml) was added and the mixture extracted with dichloromethane. The organic layer was washed with brine, dried (MgSO4) and evaporated to dryness under reduced pressure. The residue was purified by flash chromatography on silica using dichloromethane, followed by a 24:1:0.1 mixture of dichloromethane methanol: triethylamine as eluant. The product so obtained was triturated with ethyl acetate to give 3-[2-(2-methoxyethoxy)ethoxycarbonyl]-4-oxo-3,4-dihydro-1,10-phenanthroline in 68% overall yield, mp 164-165° C.

Workup

  1. stirringthe mixture stirred for 18 hours
  2. customevaporated to dryness under reduced pressure
  3. additionWater (50 ml) was added
  4. extractionthe mixture extracted with dichloromethane
  5. washThe organic layer was washed with brine
  6. dry with materialdried (MgSO4)
  7. customevaporated to dryness under reduced pressure
  8. customThe residue was purified by flash chromatography on silica
  9. additionfollowed by a 24:1:0.1 mixture of dichloromethane methanol
  10. customThe product so obtained
  11. customwas triturated with ethyl acetate

Sources & evidence

ORD record
ord-8aaf4b77c30045e7a474a5645fbfa5d4
Source dataset
uspto-grants-2001_03
Patent number
US06200974B1

Reaction notes

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