Hydrochloric Acid → HCID 66825913, compound

HRID 401083Notes

Reaction equation

HRID 401083 reaction equation
[C:1]1([CH2:7][C:8]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=2)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:20]([O:22][C:23]1[CH:24]=[C:25]([CH:28]=[C:29]([N+:32]([O-:34])=[O:33])[C:30]=1[OH:31])[CH:26]=O)[CH3:21].[NH2:35][C:36]([NH2:38])=[O:37].Cl>CCO>[CH2:20]([O:22][C:23]1[CH:24]=[C:25]([CH:26]2[C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[C:8]([C:10]3[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=3)[NH:38][C:36](=[O:37])[NH:35]2)[CH:28]=[C:29]([N+:32]([O-:34])=[O:33])[C:30]=1[OH:31])[CH3:21]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1176UreaHCID 3182342-Phenyl-1-[4-(trifluoromethyl)phenyl]ethan-1-oneHCID 5848783-Ethoxy-4-hydroxy-5-nitrobenzaldehyde

Product 1

HCID 66825913HCID 66825913, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-phenyl-1-(4-(trifluoromethyl)phenyl)ethanone (commercially available) (200 mg, 0.76 mmol), 3-ethoxy-4-hydroxy-5-nitrobenzaldehyde (145 mg, 0.69 mmol), urea (124 mg, 2.06 mmol), conc. HCl (0.06 mL, 0.69 mmol) in EtOH (5 mL) was refluxed overnight. Followed a standard aqueous/EtOAc workup, then purified by preparative HPLC to give Compound 113 (135.34 mg, yield 39%). 1H NMR (DMSO-d6 400 MHz): δ 8.83 (d, J=1.6 Hz, 1H), 7.60-7.56 (m, 3H), 7.40-7.39 (m, 3H), 7.13 (s, 1H), 7.06-7.00 (m, 3H), 6.83-6.80 (m, 2H), 5.23 (d, J=2.4 Hz, 1H), 4.06-3.97 (m, 2H), 1.30 (t, J=7.2 Hz, 3H); MS (ESI): m/z 500.0 [M+1]+.

Workup

  1. temperaturewas refluxed overnight
  2. customFollowed a standard aqueous/EtOAc workup, then purified by preparative HPLC

Sources & evidence

ORD record
ord-fa15f0706ee14d549dd128d86610d908
Source dataset
uspto-grants-2014_06
Patent number
US08741915B2

Reaction notes

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