Hydrochloric Acid → HCID 51347475, compound

HRID 924778Notes

Reaction equation

HRID 924778 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.[OH:16][C:17]1[C:24]([N+:25]([O-:27])=[O:26])=[CH:23][C:20]([CH:21]=O)=[CH:19][C:18]=1[O:28][CH3:29].[NH2:30][C:31]([NH2:33])=[O:32].Cl>C(O)C>[OH:16][C:17]1[C:24]([N+:25]([O-:27])=[O:26])=[CH:23][C:20]([CH:21]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:33][C:31](=[O:32])[NH:30]2)=[CH:19][C:18]=1[O:28][CH3:29]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1176UreaHCID 99482-PhenylacetophenoneHCID 811345-Nitrovanillin

Product 1

HCID 51347475HCID 51347475, compoundYield 41.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1,2-diphenylethanone (300 mg, 1.53 mmol), 4-hydroxy-3-methoxy-5-nitrobenzaldehyde (301 mg, 1.53 mmol), urea (275 mg, 4.587 mmol), and concentrated HCl (0.3 mL) in ethanol (10 mL) was refluxed for 80 h. After being cooled down to room temperature, the mixture was evaporated. The residue was purified by HPLC to give Compound 9 (262 mg, yield 41.1%). 1H NMR (DMSO-d6 400 MHz): δ 10.45 (s, 1H), 8.73 (s, 1H), 7.54 (s, 1H), 7.46 (s, 1H), 7.27-7.25 (m, 3H), 7.23-7.21 (m, 3H), 7.06-7.00 (m, 3H), 6.83 (d, J=6.8 Hz, 2H), 5.2 (d, J=2.4 Hz, 1H), 3.80 (s, 3H); MS (ESI): m/z 417.9 [M+1]+.

Workup

  1. temperaturewas refluxed for 80 h
  2. customthe mixture was evaporated
  3. customThe residue was purified by HPLC

Sources & evidence

ORD record
ord-ccfb16e7adf94158bff3affde498cc07
Source dataset
uspto-grants-2016_03
Patent number
US09283229B2

Reaction notes

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