N-(2,2-diethoxyethyl)-N'-(2,4-difluorophenyl)urea → 1-(2,4-difluorophenyl)-2(1H,3H)-imidazolone

HRID 129158Notes

Reaction equation

HRID 129158 reaction equation
C(O[CH:4](OCC)[CH2:5][NH:6][C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][C:11]=1[F:17])=[O:8])C>CO.O.Cl>[F:17][C:11]1[CH:12]=[C:13]([F:16])[CH:14]=[CH:15][C:10]=1[N:9]1[CH:4]=[CH:5][NH:6][C:7]1=[O:8]

Participants

5

Reactant 1

HCID 19065111N-(2,2-diethoxyethyl)-N'-(2,4-difluorophenyl)urea

Product 1

HCID 190650921-(2,4-difluorophenyl)-2(1H,3H)-imidazoloneYield 89.4%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

This urea (37.5 g) was dissolved in a mixture of 560 ml of methanol and 280 ml of water, and 300 ml of 0.48M hydrochloric acid was added thereto and the resulting mixture was stirred for three days at room temperature. The reaction solution was concentrated under reduced pressure. The crystals thus separated out were washed with a mixture of water and methanol (5:1) to give 22.8 g of 1-(2,4-difluorophenyl)-2(1H,3H)-imidazolone as a colorless powder.

Workup

  1. additionwas added
  2. concentrationThe reaction solution was concentrated under reduced pressure
  3. customThe crystals thus separated out
  4. washwere washed with a mixture of water and methanol (5:1)

Sources & evidence

ORD record
ord-8d82a73fa4cf4fb9bf2139f0d84dd2a9
Source dataset
uspto-grants-1995_11
Patent number
US05466820

Reaction notes

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