4-[2,5-Dioxo-3-methyl-4-(3-methylphenyl)-4-[(2-propenyloxy)methyl]imidazolidin-1-yl]-2-trifluoromethylbenzonitrile → 4-[2,5-Dioxo-4-hydroxymethyl-3-methyl-4-(3-methylphenyl)imidazolidin-1-yl]-2-trifluoromethylbenzonitrile

HRID 389899Notes

Reaction equation

HRID 389899 reaction equation
[O:1]=[C:2]1[N:6]([CH3:7])[C:5]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[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(Cl)Cl>[O:1]=[C:2]1[N:6]([CH3:7])[C:5]([CH2:8][OH:9])([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[CH:14]=2)[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:30])[F:31])[CH:22]=1

Participants

3

Reactant 1

HCID 671309294-[2,5-Dioxo-3-methyl-4-(3-methylphenyl)-4-[(2-propenyloxy)methyl]imidazolidin-1-yl]-2-trifluoromethylbenzonitrile

Product 1

HCID 593171864-[2,5-Dioxo-4-hydroxymethyl-3-methyl-4-(3-methylphenyl)imidazolidin-1-yl]-2-trifluoromethylbenzonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 856 mg of 4-[2,5-dioxo-3-methyl-4-(3-methylphenyl)-4-[(2-propenyloxy)methyl]imidazolidin-1-yl]-2-trifluoromethylbenzonitrile in DCM (5 mL) is added trifluoroborane-dimethylsulfide complex (812 μL). The mixture is stirred 4 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-c96206a3a0d8403db1c135f7c84ac65c
Source dataset
uspto-grants-2013_02
Patent number
US08383608B2

Reaction notes

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