1-(2,2-diethoxyethyl)-3-[4-(1H-1,2,4-triazol-1-yl)phenyl]urea → 1-[4-(1H-1,2,4-triazol-1-yl)phenyl]-2-(1H,3H)-imidazolone

HRID 279170Notes

Reaction equation

HRID 279170 reaction equation
C(O[CH:4](OCC)[CH2:5][NH:6][C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([N:16]2[CH:20]=[N:19][CH:18]=[N:17]2)=[CH:12][CH:11]=1)=[O:8])C>CO.O.Cl>[N:16]1([C:13]2[CH:12]=[CH:11][C:10]([N:9]3[CH:4]=[CH:5][NH:6][C:7]3=[O:8])=[CH:15][CH:14]=2)[CH:20]=[N:19][CH:18]=[N:17]1

Participants

5

Reactant 1

HCID 105917121-(2,2-diethoxyethyl)-3-[4-(1H-1,2,4-triazol-1-yl)phenyl]urea

Product 1

HCID 106330471-[4-(1H-1,2,4-triazol-1-yl)phenyl]-2-(1H,3H)-imidazoloneYield 77.5%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

1-(2,2-Diethoxyethyl)-3-[4-(1H-1,2,4-triazol-1-yl)phenyl]urea (14.5 g) was dissolved in a mixture of methanol (214 ml) and water (85 ml), to which diluted hydrochloric acid (0.48 M, 104 ml) was added dropwise. After the reaction solution was stirred at room temperature for 14 hours, the precipitated crystals were collected by filtration to give 1-[4-(1H-1,2,4-triazol-1-yl)phenyl]-2-(1H,3H)-imidazolone (8.0 g) as a colorless crystalline powder. The filtrate was concentrated under reduced pressure to about 200 ml and the precipitated crystals were collected by filtration to give an additional amount (1.08 g) of the product.

Workup

  1. additionwas added dropwise
  2. filtrationthe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-2f99c3258df647f4865b4fc77b17a5d6
Source dataset
uspto-grants-2002_03
Patent number
US06362206B1

Reaction notes

Loading…