Hydrochloric Acid → HCID 51347325, compound

HRID 2177868Notes

Reaction equation

HRID 2177868 reaction equation
[C:1]1([C:7](=O)[CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:16]([O:18][C:19]1[CH:20]=[C:21]([CH:24]=[C:25]([N+:28]([O-:30])=[O:29])[C:26]=1[OH:27])[CH:22]=O)[CH3:17].[NH2:31][C:32]([NH2:34])=[O:33].Cl>CCO.CO.CCOC(C)=O>[CH2:16]([O:18][C:19]1[CH:20]=[C:21]([CH:22]2[C:8]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)=[C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[NH:34][C:32](=[O:33])[NH:31]2)[CH:24]=[C:25]([N+:28]([O-:30])=[O:29])[C:26]=1[OH:27])[CH3:17]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 1176UreaHCID 99482-PhenylacetophenoneHCID 5848783-Ethoxy-4-hydroxy-5-nitrobenzaldehyde

Product 1

HCID 51347325HCID 51347325, compoundYield 49%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of compound 1,2-diphenylethanone (557 mg, 2.8 mmol), 3-ethoxy-4-hydroxy-5-nitrobenzaldehyde (500 mg, 2.4 mmol), and urea (427 mg, 7.1 mmol) in EtOH (50 mL) was added concentrated HCl (0.24 mL), and the reaction mixture was heated at reflux for three days. TLC (EtOAc:MeOH=10:1) showed that the starting materials were consumed. The reaction mixture was concentrated and purified by column chromatography (EtOAc:MeOH=30:1) to afford Compound 1 as a yellow solid (500 mg, yield: 49.0%). 1H NMR (DMSO-d6 400 MHz): δ 10.25 (s, 1H), 8.70 (s, 1H), 7.50 (s, 1H), 7.42 (d, J=2.0 Hz, 1H), 7.15-7.25 (m, 6H), 6.95-7.05 (m, 3H), 6.80 (d, J=6.4 Hz, 2H), 5.15 (d, J=2.8 Hz, 1H), 4.05 (m, 2H), 1.30 (t, J=6.8 Hz, 3H); MS (ESI): m/z 432.2 [M+1]+.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for three days
  3. customwere consumed
  4. concentrationThe reaction mixture was concentrated
  5. custompurified by column chromatography (EtOAc:MeOH=30:1)

Sources & evidence

ORD record
ord-85a420b13b954caf8c54d9992ee1bb91
Source dataset
uspto-grants-2015_06
Patent number
US09067893B2

Reaction notes

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