Sodium Bicarbonate → HCID 59317181, compound

HRID 2427131Notes

Reaction equation

HRID 2427131 reaction equation
[O:1]=[C:2]1[N:6]([CH3:7])[C:5]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)([CH2:8][O:9]CC=C)[C:4](=[O:19])[N:3]1[C:20]1[CH:27]=[CH:26][C:23]([C:24]#[N:25])=[C:22]([C:28]([F:31])([F:30])[F:29])[CH:21]=1.C(=O)(O)[O-].[Na+]>ClCCl>[O:1]=[C:2]1[N:6]([CH3:7])[C:5]([CH2:8][OH:9])([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:4](=[O:19])[N:3]1[C:20]1[CH:27]=[CH:26][C:23]([C:24]#[N:25])=[C:22]([C:28]([F:31])([F:29])[F:30])[CH:21]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 67131041HCID 67131041, compound

Product 1

HCID 59317181HCID 59317181, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 0.52 g of 4-[2,5-dioxo-3-methyl-4-phenyl-4-[(2-propenyloxy)methyl]imidazolidin-1-yl]-2-trifluoromethylbenzonitrile in 40 mL of dichloromethane is added 2 mL of trifluoroborane-dimethylsulfide complex in 10 mL of dichloromethane. The mixture is stirred at rt for 3 hours and poured into a saturated aqueous sodium bicarbonate solution and extracted with ethyl acetate. The organic layer is dried over magnesium sulfate, filtered and evaporated. The crude product is purified by chromatography over silica gel while eluting with 70/30 heptane/ethyl acetate mixture to provide the desired product.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer is dried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customThe crude product is purified by chromatography over silica gel
  6. washwhile eluting with 70/30 heptane/ethyl acetate mixture

Sources & evidence

ORD record
ord-b70f0de71e254624b0d6e96abe3ab582
Source dataset
uspto-grants-2011_06
Patent number
US07968581B2

Reaction notes

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