Sodium Bicarbonate → 4-[4-(4-Fluorophenyl)-2,5-dioxo-4-hydroxymethyl-3-(2-propynyl)imidazolidin-1-yl]-2-trifluoromethylbenzonitrile

HRID 2427139Notes

Reaction equation

HRID 2427139 reaction equation
[O:1]=[C:2]1[N:6]([CH2:7][C:8]#[CH:9])[C:5]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)([CH2:10][O:11]CC=C)[C:4](=[O:22])[N:3]1[C:23]1[CH:30]=[CH:29][C:26]([C:27]#[N:28])=[C:25]([C:31]([F:34])([F:33])[F:32])[CH:24]=1.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[F:21][C:18]1[CH:19]=[CH:20][C:15]([C:5]2([CH2:10][OH:11])[C:4](=[O:22])[N:3]([C:23]3[CH:30]=[CH:29][C:26]([C:27]#[N:28])=[C:25]([C:31]([F:34])([F:32])[F:33])[CH:24]=3)[C:2](=[O:1])[N:6]2[CH2:7][C:8]#[CH:9])=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 866414594-[2,5-Dioxo-4-(4-fluorophenyl)-4-[(2-propenyloxy)methyl]-3-(2-propynyl)imidazolidin-1-yl]-2-trifluoromethylbenzonitrile

Product 1

HCID 593171594-[4-(4-Fluorophenyl)-2,5-dioxo-4-hydroxymethyl-3-(2-propynyl)imidazolidin-1-yl]-2-trifluoromethylbenzonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.45 g of 4-[2,5-dioxo-4-(4-fluorophenyl)-4-[(2-propenyloxy)methyl]-3-(2-propynyl)imidazolidin-1-yl]-2-trifluoromethylbenzonitrile obtained in step 1 is dissolved in 5 mL of DCM under argon atmosphere. 0.2 mL of trifluoroborane-dimethylsulfide complex is added. The mixture is stirred at room temperature for 18 hours. A saturated aqueous sodium bicarbonate solution is slowly added. 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 6/1 DCM/ethyl acetate.

Workup

  1. addition0.2 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 6/1 DCM/ethyl acetate

Sources & evidence

ORD record
ord-f57ec77b50a9412e955aa7c514eb88e1
Source dataset
uspto-grants-2011_06
Patent number
US07968581B2

Reaction notes

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