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

HRID 1919298Notes

Reaction equation

HRID 1919298 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-c1d71aaff6ff47f2981f1ae9a49ce1ce
Source dataset
uspto-grants-2012_05
Patent number
US08168627B2

Reaction notes

Loading…