p-Toluenesulfonic acid → 4-[3-(3-Hydroxy-propyl)-4,4-dimethyl-2,5-dioxo-imidazolidin-1-yl]-2-trifluoromethyl-benzonitrile

HRID 2233603Notes

Reaction equation

HRID 2233603 reaction equation
[CH3:1][C:2]1([CH3:30])[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][CH2:22][CH2:23][O:24]C1CCCO1.CC1C=CC(S(O)(=O)=O)=CC=1>CO.C(OCC)(=O)C>[OH:24][CH2:23][CH2:22][CH2:21][N:3]1[C:2]([CH3:30])([CH3:1])[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]1=[O:20]

Participants

5

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 675019934-{4,4-Dimethyl-2,5-dioxo-3-[3-(tetrahydro-furan-2-yloxy)-propyl]-imidazolidin-1-yl}-2-trifluoromethyl-benzonitrile

Product 1

HCID 221169524-[3-(3-Hydroxy-propyl)-4,4-dimethyl-2,5-dioxo-imidazolidin-1-yl]-2-trifluoromethyl-benzonitrileYield 95%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of compound 12a (1.03 g, 2.33 mmol) in methanol (10 mL) at room temperature was added p-TSA (88 mg, 0.46 mmol). The solution was stirred for 3 hrs at room temperature. The reaction was then diluted with ethyl acetate (50 mL), washed successively with a 10% bicarbonate and brine solution and finally dried over magnesium sulphate to give compound 13a (786 mg, 95%) which was directly used as such in the next step. 1H NMR (300 MHz, Acetone-d6) δ: 1.57 (s, 6H), 1.92 (m, 2H), 3.54, (t, 2H, J=7.38 Hz), 3.51-3.63 (m, 2H), 8.18 (m, 2H), 8.27 (s, 1H).

Workup

  1. washwashed successively with a 10% bicarbonate and brine solution
  2. dry with materialfinally dried over magnesium sulphate

Sources & evidence

ORD record
ord-f5b1c67731b44405aa08ce522f21824e
Source dataset
uspto-grants-2010_05
Patent number
US07709516B2

Reaction notes

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