Hydrochloric Acid → HCID 51348075, compound

HRID 2177899Notes

Reaction equation

HRID 2177899 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11](=O)[CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[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>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[NH:38][C:36](=[O:37])[NH:35][CH:26]([C:25]3[CH:28]=[C:29]([N+:32]([O-:34])=[O:33])[C:30]([OH:31])=[C:23]([O:22][CH2:20][CH3:21])[CH:24]=3)[C:12]=2[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1176UreaHCID 5848783-Ethoxy-4-hydroxy-5-nitrobenzaldehydeHCID 6786631-(3,4-dimethoxyphenyl)-2-phenylethanone

Product 1

HCID 51348075HCID 51348075, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1-(3,4-dimethoxyphenyl)-2-phenylethanone (180 mg, 0.7 mmol), 3-ethoxy-4-hydroxy-5-nitrobenzaldehyde (124 mg, 0.59 mmol), urea (105 mg, 1.8 mmol), and concentrated HCl solution (0.05 mL, 0.59 mmol) in EtOH (5 mL) was refluxed overnight. The mixture was evaporated in vacuo, and the residue was purified by preparative HPLC to give Compound 38 (100 mg, yield 35%) as a yellow solid. 1H NMR (CD3OD 400 MHz): δ 7.63 (d, J=1.2 Hz, 1H), 7.19 (s, 1H), 7.13-7.06 (m, 3H), 6.93-6.85 (m, 4H), 6.73 (s, 1H), 5.34 (s, 1H), 4.11-4.02 (m, 2H), 3.80 (s, 3H), 3.57 (s, 3H), 1.41 (t, J=6.8 Hz, 3H); MS (ESI): m/z 492.0 [M+1]+.

Workup

  1. temperaturewas refluxed overnight
  2. customThe mixture was evaporated in vacuo
  3. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-08028df1e2ae4d8295f35ac79a92f9f4
Source dataset
uspto-grants-2015_06
Patent number
US09067893B2

Reaction notes

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