Hydrochloric Acid → HCID 51348665, compound

HRID 924842Notes

Reaction equation

HRID 924842 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([C:7](=O)[CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:4]=[CH:3]1.[CH2:16]([O:18][C:19]1[CH:20]=[C:21]([CH:24]=[C:25]([N+:28]([O-:30])=[O:29])[C:26]=1[OH:27])[CH:22]=O)[CH3:17].[NH2:31][C:32]([NH2:34])=[O:33].Cl>CCO>[CH2:16]([O:18][C:19]1[CH:20]=[C:21]([CH:22]2[C:8]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)=[C:7]([C:5]3[N:4]=[CH:3][N:2]([CH3:1])[CH:6]=3)[NH:34][C:32](=[O:33])[NH:31]2)[CH:24]=[C:25]([N+:28]([O-:30])=[O:29])[C:26]=1[OH:27])[CH3:17]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1176UreaHCID 5848783-Ethoxy-4-hydroxy-5-nitrobenzaldehydeHCID 67061131HCID 67061131, compound2×

Product 1

HCID 51348665HCID 51348665, compoundYield 30.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1-(1-methyl-1H-imidazol-4-yl)-2-phenylethanone (Intermediate 40) (130 mg, 0.65 mmol), compound 3-ethoxy-4-hydroxy-5-nitrobenzaldehyde (165 mg, 0.78 mmol), and urea (117 mg, 1.95 mmol) in anhydrous EtOH (5 mL) was added concentrated HCl solution (0.2 mL), the reaction mixture was refluxed for 16 hours. The reaction mixture was concentrated under reduced pressure, and purified by column chromatograph and preparative HPLC to afford Compound 80 as a yellow solid (87 mg, yield: 30.8%). 1H NMR (DMSO-d6 400 MHz): δ 10.31 (s, 1H), 8.62 (m, 2H), 7.68 (s, 1H), 7.37 (d, J=2.0 Hz, 1H), 7.19-7.22 (m, 3H), 7.06 (m, 2H), 6.97-7.00 (m, 2H), 5.25 (d, J=2.4 Hz, 1H), 3.95-4.07 (m, 2H), 3.67 (s, 3H), 1.29-1.33 (t, J=6.8 Hz, 3H); MS (ESI): m/z 436.1 [M+1]+.

Workup

  1. temperaturethe reaction mixture was refluxed for 16 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. custompurified by column chromatograph and preparative HPLC

Sources & evidence

ORD record
ord-02360a338e154b049f4b39b6d4eed338
Source dataset
uspto-grants-2016_03
Patent number
US09283229B2

Reaction notes

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