Sodium Bicarbonate → 4-[2,5-Dioxo-4-(4-fluorophenyl)-4-hydroxymethyl-3-methylimidazolidin-1-yl]-2-trifluoromethylbenzonitrile

HRID 2427137Notes

Reaction equation

HRID 2427137 reaction equation
[O:1]=[C:2]1[N:6]([CH3:7])[C:5]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)([CH2:8][O:9]CC=C)[C:4](=[O:20])[N:3]1[C:21]1[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[C:23]([C:29]([F:32])([F:31])[F:30])[CH:22]=1.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[O:1]=[C:2]1[N:6]([CH3:7])[C:5]([C:13]2[CH:14]=[CH:15][C:16]([F:19])=[CH:17][CH:18]=2)([CH2:8][OH:9])[C:4](=[O:20])[N:3]1[C:21]1[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[C:23]([C:29]([F:31])([F:32])[F:30])[CH:22]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 671309984-[2,5-Dioxo-4-(4-fluorophenyl)-3-methyl-4-[(2-propenyloxy)methyl]imidazolidin-1-yl]-2-trifluoromethylbenzonitrile

Product 1

HCID 593171844-[2,5-Dioxo-4-(4-fluorophenyl)-4-hydroxymethyl-3-methylimidazolidin-1-yl]-2-trifluoromethylbenzonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The crude mixture of 4-[2,5-dioxo-4-(4-fluorophenyl)-3-methyl-4-[(2-propenyloxy)methyl]imidazolidin-1-yl]-2-trifluoromethylbenzonitrile obtained in step 5 is solubilised in 5 mL of DCM under argon atmosphere. 0.9 mL of trifluoroborane-dimethylsulfide complex is added. The mixture is stirred at rt for 7 hours. A saturated aqueous sodium bicarbonate solution is added slowly, the product is extracted with DCM and the organic layer is dried over sodium sulfate, filtered and evaporated. The crude product is purified by chromatography over silica gel while eluting with 4/1 DCM/ethyl acetate.

Workup

  1. addition0.9 mL of trifluoroborane-dimethylsulfide complex is added
  2. extractionthe product is extracted with DCM
  3. dry with materialthe organic layer is dried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude product is purified by chromatography over silica gel
  7. washwhile eluting with 4/1 DCM/ethyl acetate

Sources & evidence

ORD record
ord-236e94d852c04353be1375598097a173
Source dataset
uspto-grants-2011_06
Patent number
US07968581B2

Reaction notes

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