Hydrochloric Acid → HCID 51349080, compound

HRID 2177966Notes

Reaction equation

HRID 2177966 reaction equation
[C:1]1([CH2:7][C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[CH3:16])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:17]([O:19][C:20]1[CH:21]=[C:22]([CH:25]=[C:26]([N+:29]([O-:31])=[O:30])[C:27]=1[OH:28])[CH:23]=O)[CH3:18].[NH2:32][C:33]([NH2:35])=[O:34].Cl>CCO.CCOC(C)=O>[CH2:17]([O:19][C:20]1[CH:21]=[C:22]([CH:23]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][CH:13]=[CH:12][C:11]=3[CH3:16])[NH:35][C:33](=[O:34])[NH:32]2)[CH:25]=[C:26]([N+:29]([O-:31])=[O:30])[C:27]=1[OH:28])[CH3:18]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1176UreaHCID 5848783-Ethoxy-4-hydroxy-5-nitrobenzaldehydeHCID 66133131-(2-Methylphenyl)-2-phenylethan-1-one

Product 1

HCID 51349080HCID 51349080, compoundYield 8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-phenyl-1-o-tolylethanone (commercially available) (200 mg, 0.95 mmol), 3-ethoxy-4-hydroxy-5-nitrobenzaldehyde (183 mg, 0.86 mmol), urea (156 mg, 2.59 mmol), concentrated HCl (0.07 mL, 0.86 mmol) in EtOH (5 mL) was refluxed overnight. Followed standard aqueous/EtOAc workup, then purified by preparative HPLC to give Compound 114 (31.75 mg, yield 8%). 1H NMR (DMSO-d6 400 MHz): δ 10.33 (br, 1H), 8.59 (s, 1H), 7.51-7.44 (m, 2H), 7.23-7.13 (m, 4H), 6.96-6.89 (m, 4H), 6.80-6.77 (m, 2H), 5.36-5.21 (m, 1H), 4.08-3.99 (m, 2H), 2.36 (s, 1.6H), 2.13 (s, 1.3H), 1.34-1.28 (m, 3H); MS (ESI): m/z 446.0 [M+1]+.

Workup

  1. temperaturewas refluxed overnight
  2. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-4c339bc1f467418bb37ed1e2fd04c923
Source dataset
uspto-grants-2015_06
Patent number
US09067893B2

Reaction notes

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