Acetic Acid → 4-{4,4-Dimethyl-3-[2-(methylphenylamino)benzyl]-2,5-dioxoimidazolidin-1-yl}-2-trifluoromethylbenzonitrile

HRID 2356666Notes

Reaction equation

HRID 2356666 reaction equation
[CH3:1][C:2]1([CH3:35])[C:6](=[O:7])[N:5]([C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[C:10]([C:16]([F:19])([F:18])[F:17])[CH:9]=2)[C:4](=[O:20])[N:3]1[CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[NH:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.[C:36]([BH3-])#N.[Na+].C=O.C(O)(=O)C>C(#N)C>[CH3:1][C:2]1([CH3:35])[C:6](=[O:7])[N:5]([C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[C:10]([C:16]([F:19])([F:17])[F:18])[CH:9]=2)[C:4](=[O:20])[N:3]1[CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[N:28]([CH3:36])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 712Formaldehyde2×HCID 5003444Sodium cyanoborohydride2×HCID 578293104-[4,4-Dimethyl-2,5-dioxo-3-(2-phenylaminobenzyl)imidazolidin-1-yl]-2-trifluoromethylbenzonitrile

Product 1

HCID 578293254-{4,4-Dimethyl-3-[2-(methylphenylamino)benzyl]-2,5-dioxoimidazolidin-1-yl}-2-trifluoromethylbenzonitrileYield 60%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

53 mg of the compound of example 1 were dissolved in 1.1 ml of acetonitrile. 10.4 mg of sodium cyanoborohydride were added to this solution. Subsequently, 0.18 ml of a 37% formalin solution and 0.05 ml of glacial acetic acid were added dropwise. The mixture was stirred at room temperature for 2 h; thereafter and another 2 h later, the same amounts of sodium cyanoborohydride and formalin solution were once again added dropwise. For workup, the mixture was filtered through a silica gel cartridge and the filtrate was concentrated under reduced pressure and purified by chromatography (method [RP1]). 4-{4,4-Dimethyl-3-[2-(methylphenylamino)benzyl]-2,5-dioxoimidazolidin-1-yl}-2-trifluoromethylbenzonitrile 59 was obtained in a yield of 60%. Molecular weight 492.17 (C27H23F3N4O2); retention time Rt=2.33 min. [B]; MS (ESI): 493.05 (MH+).

Workup

  1. filtrationFor workup, the mixture was filtered through a silica gel cartridge
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. custompurified by chromatography (method [RP1])

Sources & evidence

ORD record
ord-7825d396fcb24d13b986f921f6844c18
Source dataset
uspto-grants-2010_07
Patent number
US07759366B2

Reaction notes

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