Hydrochloric Acid → HCID 56961405, compound

HRID 401068Notes

Reaction equation

HRID 401068 reaction equation
[C:1]1([C:7](=O)[CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:16]([C:18]1[CH:19]=[C:20]([CH:24]=[CH:25][CH:26]=1)[C:21]([OH:23])=[O:22])=O.[NH2:27][C:28]([NH2:30])=[O:29].Cl>CCO>[O:29]=[C:28]1[NH:30][CH:16]([C:18]2[CH:19]=[C:20]([CH:24]=[CH:25][CH:26]=2)[C:21]([OH:23])=[O:22])[C:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[NH:27]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1176UreaHCID 99482-PhenylacetophenoneHCID 120773-Carboxybenzaldehyde

Product 1

HCID 56961405HCID 56961405, compoundYield 15.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of 1,2-diphenylethanone (784 mg, 4.0 mmol), 3-formylbenzoic acid (500 mg, 3.33 mmol) and urea (600 mg, 10.0 mmol) in EtOH (40 mL) was added concentrated HCl (1.6 mL). The mixture was stirred at 85° C. for 3 days. The volatiles were removed under reduced pressure and standard aqueous/EtOAc workup procedure was followed. Purification by column chromatography (100% EA) gave Compound 93 as an off-white powder (186 mg, 15%). 1H NMR (DMSO-d6 500 MHz): δ 8.70 (s, 1H), 7.99 (s, 1H), 7.83 (d, J=7.5 Hz, 1H), 7.57 (s, 2H), 7.50 (t, J=14.5 Hz, 1H), 7.21-7.25 (m, 5H), 6.79-7.02 (m, 3H), 6.78 (d, J=7.0 Hz, 2H), 5.24 (d, J=2.0 Hz, 1H); MS (ESI): m/z 371.1 [M+1]+.

Workup

  1. customThe volatiles were removed under reduced pressure
  2. customPurification by column chromatography (100% EA)

Sources & evidence

ORD record
ord-fdf18c9f8bf045c789ad1d26831325d7
Source dataset
uspto-grants-2014_06
Patent number
US08741915B2

Reaction notes

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