Hydrochloric Acid → HCID 51347626, compound

HRID 2177883Notes

Reaction equation

HRID 2177883 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=O)[CH:5]=[CH:6][CH:7]=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.CO.CCOC(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:23]([C:22]3[CH:25]=[C:26]([N+:29]([O-:31])=[O:30])[C:27]([OH:28])=[C:20]([O:19][CH2:17][CH3:18])[CH:21]=3)[NH:32][C:33](=[O:34])[NH:35][C:9]=2[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 1176UreaHCID 2466012-(3-chlorophenyl)-1-phenylethanoneHCID 5848783-Ethoxy-4-hydroxy-5-nitrobenzaldehyde

Product 1

HCID 51347626HCID 51347626, compoundYield 22.3%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 2-(3-chlorophenyl)-1-phenylethanone (200 mg, 0.88 mmol), 3-ethoxy-4-hydroxy-5-nitrobenzaldehyde (220 mg, 1.04 mmol), and urea (159 mg, 2.65 mmol) in anhydrous EtOH (20 mL) was added concentrated HCl solution (0.1 mL), and the reaction mixture was refluxed for three days. When TLC (EtOAc:MeOH=10:1) showed that about 50% of starting materials were consumed, the reaction mixture was concentrated and purified by column chromatography (EtOAc:MeOH=40:1) and preparative HPLC to afford Compound 21 as a yellow solid (90 mg, yield 22.3%). 1H NMR (DMSO-d6 400 MHz): δ 10.30 (s, 1H), 8.81 (s, 1H), 7.60 (s, 1H), 7.45 (s, 1H), 7.25 (d, J=4.0 Hz, 3H), 7.15-7.25 (m, 3H), 7.03 (d, J=4.8 Hz, 2H), 6.71-6.81 (m, 2H), 5.25 (s, 1H), 4.00-4.10 (m, 2H), 1.33 (t, J=6.8 Hz, 3H); MS (ESI): m/z 466.0 [M+1]+.

Workup

  1. temperaturethe reaction mixture was refluxed for three days
  2. customwere consumed
  3. concentrationthe reaction mixture was concentrated
  4. custompurified by column chromatography (EtOAc:MeOH=40:1) and preparative HPLC

Sources & evidence

ORD record
ord-3d7d441cbcce48e0826eb8a4cec6b28d
Source dataset
uspto-grants-2015_06
Patent number
US09067893B2

Reaction notes

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