HCID 60970640, compound → HCID 13665722, compound

HRID 1987958Notes

Reaction equation

HRID 1987958 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([NH:12][CH2:13][C:14](=O)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8]>Cl>[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[C:14]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:13][NH:12][C:10]2=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

3

Reactant 1

HCID 60970640HCID 60970640, compound

Product 1

HCID 13665722HCID 13665722, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

250 mL of concentrated HCl were added 1-(3,4-dichloro-phenyl)-3-(2-oxo-2-phenyl-ethyl)urea (1 equiv., 56 mmol, 18.0 g) at room temperature. The reaction mixture was stirred for one week until starting material disappeared giving a white foam which was filtered off. This foam was purified by recrystallization in ethanol affording 1-(3,4-dichloro-phenyl)-5-phenyl-1,3-dihydro-imidazol-2-one (14.4 g, 85%) as a white solid. Rf 0.2 (n-heptane/ethyl acetate 2:1). δH NMR (DMSO, 300 MHz) 10.68 (1H, br s, NH), 7.62 (1H, d, J=8.6 Hz, H arom), 7.53 (1H, d, J=2.4 Hz, H arom), 7.32-7.20 (3H, m, H arom), 7.09-7.06 (2H, m, H arom), 7.03 (1H, dd, J=8.6, 2.5 Hz, H arom), 6.89 (1H, s, ═CH); m/z (EI) 309.2 (21%), 307.2 (97), 306.1 (24), 305.1 (100, M+H+).

Workup

  1. customdisappeared giving a white foam which
  2. filtrationwas filtered off
  3. customThis foam was purified by recrystallization in ethanol

Sources & evidence

ORD record
ord-bdfb06597cf649528d02b1a42959f23a
Source dataset
uspto-grants-2009_06
Patent number
US07553862B2

Reaction notes

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