HCID 67130990, compound → 4-[4-(3-Cyanophenyl)-2,5-dioxo-4-hydroxymethyl-3-methylimidazolidin-1-yl]-2-trifluoromethylbenzonitrile

HRID 389889Notes

Reaction equation

HRID 389889 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([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:6]=[CH:7][CH:8]=1)#[N:2]>C(Cl)Cl>[C:1]([C:3]1[CH:4]=[C:5]([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:6]=[CH:7][CH:8]=1)#[N:2]

Participants

3

Reactant 1

HCID 67130990HCID 67130990, compound

Product 1

HCID 593171714-[4-(3-Cyanophenyl)-2,5-dioxo-4-hydroxymethyl-3-methylimidazolidin-1-yl]-2-trifluoromethylbenzonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

328 μL of trifluoroborane-dimethylsulfide complex are added to a solution of 354 mg of 4-[4-(3-cyanophenyl)-2,5-dioxo-3-methyl-4-[(2-propenyloxy)methyl]imidazolidin-1-yl]-2-trifluoromethylbenzonitrile (in DCM (5 mL. The mixture is stirred 6 hours at room temperature, 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-946c53cbcc514c9ca9a04be532bb2548
Source dataset
uspto-grants-2013_02
Patent number
US08383608B2

Reaction notes

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