Hydrochloric Acid → HCID 51347476, compound

HRID 2177873Notes

Reaction equation

HRID 2177873 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[C:9]=1[OH:10])[CH:5]=O.[C:14]1([C:20](=O)[CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[NH2:29][C:30]([NH2:32])=[O:31].Cl>C(O)C>[OH:1][C:2]1[CH:3]=[C:4]([CH:5]2[C:21]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[C:20]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[NH:32][C:30](=[O:31])[NH:29]2)[CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[C:9]=1[OH:10]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1176UreaHCID 99482-PhenylacetophenoneHCID 57489573,4-Dihydroxy-5-nitrobenzaldehyde

Product 1

HCID 51347476HCID 51347476, compoundYield 12.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of 3,4-dihydroxy-5-nitrobenzaldehyde (196 mg, 1.0 mmol), 1,2-diphenylethanone (183 mg, 1.0 mmol) and urea (180 mg, 3.0 mmol) in ethanol (50 mL) was added concentrated HCl (0.2 mL) and the reaction solution was heated to reflux for three days. The reaction solution was concentrated in vacuo and purified by silica gel column chromatography (DCM:THF=20:1) to afford Compound 10 as a yellow solid (49.7 mg, 12.3%). 1H NMR (DMSO-d6 500 MHz): δ 10.23 (br, 1H), 8.72 (s, 1H), 7.51 (s, 1H), 7.20-7.28 (m, 7H), 6.81-7.04 (m, 3H), 6.80 (d, J=6.5 Hz, 2H), 5.08 (s, 1H); MS (ESI): m/z 404 [M+1]+.

Workup

  1. temperaturethe reaction solution was heated
  2. temperatureto reflux for three days
  3. concentrationThe reaction solution was concentrated in vacuo
  4. custompurified by silica gel column chromatography (DCM:THF=20:1)

Sources & evidence

ORD record
ord-669c11c29eeb4189aac69ddda62f88e9
Source dataset
uspto-grants-2015_06
Patent number
US09067893B2

Reaction notes

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