Sodium Bicarbonate → HCID 59235182, compound

HRID 1919781Notes

Reaction equation

HRID 1919781 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C@:9]2([CH3:28])[C:13](=[O:14])[N:12]([C:15]3[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[C:17]([C:23]([F:26])([F:25])[F:24])[CH:16]=3)[C:11](=[O:27])[NH:10]2)=[CH:5][CH:4]=1.C(=O)(O)[O-].[Na+]>ClCCl>[OH:2][C:3]1[CH:4]=[CH:5][C:6]([C@:9]2([CH3:28])[C:13](=[O:14])[N:12]([C:15]3[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[C:17]([C:23]([F:26])([F:25])[F:24])[CH:16]=3)[C:11](=[O:27])[NH:10]2)=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 59235259HCID 59235259, compound

Product 1

HCID 59235182HCID 59235182, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5 g of (R)-4-[4-(4-methoxyphenyl)-4-methyl-2,5-dioxoimidazolidin-1-yl]-2-trifluoromethylbenzonitrile are dissolved in 50 mL of dichloromethane. 14 mL of boron trifluoride/dimethylsulphide complex are added and the mixture is stirred overnight at AT. It is then poured in an aqueous solution of sodium bicarbonate and the product is extracted with dichloromethane. After drying over magnesium sulphate then evaporation of the solvent, the crude product is purified over a silica gel column (eluent 50/50 heptane/ethyl acetate) to provide 3.5 g of a slightly brown solid.

Workup

  1. addition14 mL of boron trifluoride/dimethylsulphide complex are added
  2. extractionthe product is extracted with dichloromethane
  3. dry with materialAfter drying over magnesium sulphate
  4. customevaporation of the solvent
  5. customthe crude product is purified over a silica gel column (eluent 50/50 heptane/ethyl acetate)
  6. customto provide 3.5 g of a slightly brown solid

Sources & evidence

ORD record
ord-0a3506b50bcc47609d440c3cb3b22010
Source dataset
uspto-grants-2012_05
Patent number
US08168667B2

Reaction notes

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