Bicarbonate Ion → 4-(4,4-Dimethyl-2,5-dioxoimidazolidin-1-yl)-2-trifluoromethylbenzonitrile

HRID 2233601Notes

Reaction equation

HRID 2233601 reaction equation
[CH3:1][C:2]1([CH3:21])[C:6](=N)[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])[NH:3]1.C(=O)(O)[O-:23]>Cl>[CH3:1][C:2]1([CH3:21])[C:6](=[O:23])[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])[NH:3]1

Participants

4

Reactant 2

HCID 769Bicarbonate IonHCID 221169484-(4,4-Dimethyl-5-imino-2-oxo-1-imidazolidinyl)-2-trifluoromethyl-benzonitrile

Product 1

HCID 111622854-(4,4-Dimethyl-2,5-dioxoimidazolidin-1-yl)-2-trifluoromethylbenzonitrileYield 95%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A suspension of the compound 10a in 6N HCl (25 mL) was refluxed for 35 min. The cooled solution was poured in a 10% bicarbonate solution, extracted using ethyl acetate (3×25 mL). The organic layer was washed with brine, and finally dried over magnesium sulphate to give of desired compound 11a (950 mg, 95%) which was used as such in the next step. 1H NMR (300 MHz, Acetone-d6) δ: 1.54 (s, 6H), 7.81 (broad s, 1H), 8.17 (m, 2H), 8.26 (s, 1H).

Workup

  1. temperaturewas refluxed for 35 min
  2. extractionextracted
  3. washThe organic layer was washed with brine
  4. dry with materialfinally dried over magnesium sulphate

Sources & evidence

ORD record
ord-4003bb6ba2654d479da2c1fed01a4d89
Source dataset
uspto-grants-2010_05
Patent number
US07709516B2

Reaction notes

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