Sulfuric Acid → 1-(5-Chloro-2-methoxyphenyl)-1,3-dihydro-2H-imidazol-2-one

HRID 650042Notes

Reaction equation

HRID 650042 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:21][CH3:22])=[C:6]([NH:8][C:9]([NH:11][CH2:12][C:13](=O)C2C=CC=CC=2)=[O:10])[CH:7]=1.S(=O)(=O)(O)O.[K+].[Br-]>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:21][CH3:22])=[C:6]([N:8]2[CH:13]=[CH:12][NH:11][C:9]2=[O:10])[CH:7]=1

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 253877Potassium BromideHCID 21714202N-(5-Chloro-2-methoxyphenyl)-N'-(2-oxo-2-phenylethyl)urea

Product 1

HCID 217142611-(5-Chloro-2-methoxyphenyl)-1,3-dihydro-2H-imidazol-2-one

Procedure

N-(5-Chloro-2-methoxyphenyl)-N′-(2-oxo-2-phenylethyl) urea (4 g, 12.7 mmol) was added to cold (0° C.) concentrated sulfuric acid and stirred for 3 h. The reaction mixture was poured into ice water (2 vol), and extracted with ethyl acetate, washed with saturated NaHCO3 solution and brine before drying over MgSO4. Recrystallization from diethylether/acetonitrile gave 1.35 g (36%). mp 133-134° C.; IR(KBr, υ=cm−1) 2962, 1628, 1576, 1236, 1144, 1130; 1H NMR (300 MHz, CDCl3) δ 3.90 (3H, s), 6.77 (1H, d, J=8.6 Hz), 6.91 (1H, dd, J=8.6 Hz, 2.5 Hz), 7.16 (1H, s), 7.22-7.27 (1H, m), 7.35-7.40 (2H, m), 7.51-7.55 (3H, m), 8.29 (1H, d, J=2.5 Hz); MS(DCl)m/z: 301 (MH+); Anal. calcd. for C16H13ClN2O2: C, 63.90; H, 4.36; N, 9.31. Found: C, 63.66; H, 4.30; N, 9.21.

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with saturated NaHCO3 solution and brine
  3. dry with materialbefore drying over MgSO4
  4. customRecrystallization from diethylether/acetonitrile
  5. customgave 1.35 g (36%)

Sources & evidence

ORD record
ord-e8d5aea6b1104d15ba9e24527b9a7cae
Source dataset
uspto-grants-2001_08
Patent number
US06271249B1

Reaction notes

Loading…