4-[4-(4-Cyanophenyl)-2,5-dioxo-3-methyl-4-[(2-propenyloxy)methyl]imidazolidin-1-yl]-2-trifluoromethylbenzonitrile → 4-[4-(4-Cyanophenyl)-2,5-dioxo-4-hydroxymethyl-3-methylimidazolidin-1-yl]-2-trifluoromethylbenzonitrile

HRID 389884Notes

Reaction equation

HRID 389884 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2([CH2:29][O:30]CC=C)[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])[N:10]2[CH3:28])=[CH:5][CH:4]=1)#[N:2]>C(Cl)Cl>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2([CH2:29][OH:30])[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:24])[F:25])[CH:16]=3)[C:11](=[O:27])[N:10]2[CH3:28])=[CH:5][CH:4]=1)#[N:2]

Participants

3

Reactant 1

HCID 671309124-[4-(4-Cyanophenyl)-2,5-dioxo-3-methyl-4-[(2-propenyloxy)methyl]imidazolidin-1-yl]-2-trifluoromethylbenzonitrile

Product 1

HCID 593171794-[4-(4-Cyanophenyl)-2,5-dioxo-4-hydroxymethyl-3-methylimidazolidin-1-yl]-2-trifluoromethylbenzonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 433 mg of 4-[4-(4-cyanophenyl)-2,5-dioxo-3-methyl-4-[(2-propenyloxy)methyl]imidazolidin-1-yl]-2-trifluoromethylbenzonitrile obtained in Step 5 in DCM (5 mL), 600 μL of boron trifluoride-dimethyl sulfide complex is added. The mixture is stirred 8 hours at rt, diluted with DCM, washed with an aqueous solution of sodium bicarbonate, dried over magnesium sulfate, concentrated and purified on silica gel (ethyl acetate/cyclohexane: 0/100 to 50/50) to give the desired compound.

Workup

  1. washwashed with an aqueous solution of sodium bicarbonate
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated
  4. custompurified on silica gel (ethyl acetate/cyclohexane: 0/100 to 50/50)

Sources & evidence

ORD record
ord-3b59fc63884c4ebeaae111d8f9de7dcd
Source dataset
uspto-grants-2013_02
Patent number
US08383608B2

Reaction notes

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