Water → 1-{4-[4-(4-Methoxyphenyl)piperazin-1-yl]phenyl}-3-(propan-2-yl)imidazolidin-2-one

HRID 1972100Notes

Reaction equation

HRID 1972100 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][N:12]([C:15]3[CH:20]=[CH:19][C:18]([NH:21][C:22]([N:24]([CH2:28][CH2:29]C)[CH2:25][CH2:26]O)=[O:23])=[CH:17][CH:16]=3)[CH2:11][CH2:10]2)=[CH:5][CH:4]=1.[CH3:31]C(C)([O-])C.[K+].C1(C)C=CC(S(Cl)(=O)=O)=CC=1.O>O1CCCC1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][N:12]([C:15]3[CH:20]=[CH:19][C:18]([N:21]4[CH2:29][CH2:28][N:24]([CH:25]([CH3:26])[CH3:31])[C:22]4=[O:23])=[CH:17][CH:16]=3)[CH2:11][CH2:10]2)=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 23665647Potassium tert-butoxideHCID 68492608HCID 68492608, compound

Product 1

HCID 137323741-{4-[4-(4-Methoxyphenyl)piperazin-1-yl]phenyl}-3-(propan-2-yl)imidazolidin-2-oneYield 76.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a slurry of N-[4-[4-(4-methoxyphenyl)-1-piperazinyl]-phenyl]-N′-2-methylethyl-N′-[2-hydroxyethyl]urea (Formula Va, 35.0 mmol, 14.4 g) in tetrahydrofuran (600 mL) was added potassium tert-butoxide (123.0 mmol, 11.2 g). The reaction vessel was cooled in an ice bath and a tetrahydrofuran (200 mL) solution of p-toluenesulfonyl chloride (57.0 mmol, 10.9 g) was added over a period of 0.5 hours. The resulting beige mixture was allowed to stir at ambient temperature for 14 hours before addition of water (200 mL). The mixture was filtered and the product was washed with water (200 mL) and dried. A white powder of 1-[4-[4-(4-methoxyphenyl)-1-piperazinyl]phenyl]-3-(1-methylethyl)-2-oxoimidazolidine (10.6 g) was obtained in 77% overall yield from 4-[4-(4-methoxyphenyl)-1-piperazinyl]benzenamine. 1H NMR (400 MHz, CDCl3) δ 7.46 (d, J=9.2 Hz, 2 H, Ar), 6.96 (d, J=9.2 Hz, 2 H, Ar), 6.95 (d, J=9.2 Hz, 2 H, Ar), 6.86 (d, J=9.2 Hz, 2 H, Ar), 4.30-4.20 (m, 1 H, CH), 3.76 (s, 3 H, OCH3), 3.82-3.72 (m, 2 H, CH2), 3.45-3.38 (m, 2 H, CH2), 3.32-3.20 (m, 8 H, CH2). The product was shown by HPLC retention time and NMR spectroscopy to be identical to an authentic standard prepared by the literature procedure. More importantly, the product of the present invention was demonstrated by HPLC to be purer (99.97 area %) relative to that of material prepared by the literature procedure (99.39 area %). Furthermore the product of the present invention did not contain the impurity which may negatively impact the quality of Pramiconazole, and which was present in material prepared by the literature procedure.

Workup

  1. temperatureThe reaction vessel was cooled in an ice bath
  2. filtrationThe mixture was filtered
  3. washthe product was washed with water (200 mL)
  4. customdried

Sources & evidence

ORD record
ord-5fd8512b4e6245f6b8ae72bd3ca27c3c
Source dataset
uspto-grants-2013_04
Patent number
US08431699B2

Reaction notes

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