Urea → HCID 67061117, compound

HRID 401110Notes

Reaction equation

HRID 401110 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][C:3]=1[F:10].[C:11]1([C:17](=O)[CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[NH2:26][C:27]([NH2:29])=[O:28]>C(O)C>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]2[C:18]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[C:17]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[NH:29][C:27](=[O:28])[NH:26]2)=[CH:4][C:3]=1[F:10]

Participants

5

Reactant 3

HCID 1176UreaHCID 99482-PhenylacetophenoneHCID 27834114-Bromo-3-fluorobenzaldehyde

Product 1

HCID 67061117HCID 67061117, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of 4-bromo-3-fluorobenzaldehyde (100 mg, 0.5 mmol), 1,2-diphenylethanone (118 mg, 0.6 mmol) and urea (90 mg, 1.5 mmol) in ethanol (3 mL) was added conc. HCL (0.1 mL). The mixture was refluxed under N2 atmosphere for 6 hrs. Solvent was removed; purified by silica gel column chromatography (PE:EtOAc=10:1 to PE:EtOAc=1:1) to give product (130 mg, yield 62%). 1H NMR (DMSO-d6 400 MHz): δ 8.74 (s, 1H), 7.74-7.68 (m, 1H), 7.54 (s, 1H), 7.26-7.15 (m, 7H), 7.03-6.95 (m, 3H), 6.81-6.79 (m, 2H), 5.24 (d, J=2.8 Hz, 1H).

Workup

  1. additionwas added conc. HCL (0.1 mL)
  2. temperatureThe mixture was refluxed under N2 atmosphere for 6 hrs
  3. customSolvent was removed
  4. custompurified by silica gel column chromatography (PE:EtOAc=10:1 to PE:EtOAc=1:1)

Sources & evidence

ORD record
ord-3a1fe8d44e9743f89701b473eab9d7e0
Source dataset
uspto-grants-2014_06
Patent number
US08741915B2

Reaction notes

Loading…