Hydrochloric Acid → HCID 66825067, compound

HRID 924848Notes

Reaction equation

HRID 924848 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]=[CH:20][C:21]([OH:27])=[C:22]([CH:26]=1)[C:23]([OH:25])=[O:24])=O.[NH2:28][C:29]([NH2:31])=[O:30].Cl>CCO>[OH:27][C:21]1[CH:20]=[CH:19][C:18]([CH:16]2[C:8]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)=[C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[NH:31][C:29](=[O:30])[NH:28]2)=[CH:26][C:22]=1[C:23]([OH:25])=[O:24]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1176UreaHCID 99482-PhenylacetophenoneHCID 692265-Formylsalicylic acid

Product 1

HCID 66825067HCID 66825067, compoundYield 10.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of 1,2-diphenylethanone (200 mg, 1.03 mmol), 5-formyl-2-hydroxybenzoic acid (203 mg, 1.22 mmol), and urea (184 mg, 3.06 mmol) in anhydrous EtOH was added concentrated HCl solution (105 mg, 1.03 mmol). The reaction was refluxed for three days. The reaction mixture was concentrated, and purified by column chromatography and preparative HPLC to give Compound 86 as an off-white solid (40 mg, yield 10.2%). 1H NMR (DMSO-d6 400 MHz): δ 11.20 (s, 1H), 8.63 (s, 1H), 7.78 (d, J=2.4 Hz, 1H), 7.42-7.50 (m, 2H), 7.13-7.28 (m, 5H), 6.90-7.00 (m, 4H), 6.75 (d, J=6.4 Hz, 2H), 5.10 (d, J=2.4 Hz, 1H); MS (ESI): m/z 387.1 [M+1]+.

Workup

  1. temperatureThe reaction was refluxed for three days
  2. concentrationThe reaction mixture was concentrated
  3. custompurified by column chromatography and preparative HPLC

Sources & evidence

ORD record
ord-adc4a834831a4c8f8dd0749b9b942898
Source dataset
uspto-grants-2016_03
Patent number
US09283229B2

Reaction notes

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