Hydrochloric Acid → HCID 51347328, compound

HRID 2177871Notes

Reaction equation

HRID 2177871 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:9]=[C:10]([N+:13]([O-:15])=[O:14])[C:11]=1[OH:12])[CH:7]=O)[CH3:2].[C:16]1([C:22](=O)[CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[NH2:31][C:32]([NH2:34])=[S:33].Cl>C(O)C>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:7]2[C:23]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[C:22]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[NH:34][C:32](=[S:33])[NH:31]2)[CH:9]=[C:10]([N+:13]([O-:15])=[O:14])[C:11]=1[OH:12])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 99482-PhenylacetophenoneHCID 5848783-Ethoxy-4-hydroxy-5-nitrobenzaldehydeHCID 2723790Thiourea

Product 1

HCID 51347328HCID 51347328, compoundYield 2.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
78 °C

Procedure

A mixture of 3-ethoxy-4-hydroxy-5-nitrobenzaldehyde (323 mg, 1.53 mmol), 1,2-diphenylethanone (300 mg, 1.53 mmol), thiourea (349.16 mg, 4.59 mmol), concentrated HCl solution (0.8 mL) in ethanol (10 mL) was refluxed at 78° C. for 76 h. After being cooled down to room temperature, the mixture was evaporated under reduced pressure, and the residue was purified by preparative HPLC to give Compound 8 (20 mg, yield 2.9%). 1H NMR (CD3CN): δ 7.68 (s, 1H), 7.65 (s, 1H), 7.31 (m, 4H), 7.21 (s, 1H), 7.09 (m, 3H), 6.94 (m, 2H), 5.34 (s, 1H), 4.11 (q, J=7.2 Hz, 2H), 1.43-1.40 (t, J=7.2 Hz, 3H); MS (ESI): m/z 447.9 [M+1]+.

Workup

  1. temperatureAfter being cooled down to room temperature
  2. customthe mixture was evaporated under reduced pressure
  3. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-6cd53821f1cd404d85c08dfc35268bda
Source dataset
uspto-grants-2015_06
Patent number
US09067893B2

Reaction notes

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