Hydrochloric Acid → HCID 51348810, compound

HRID 401065Notes

Reaction equation

HRID 401065 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:26]=[CH:25][C:21]([C:22]([OH:24])=[O:23])=[CH:20][CH:19]=1)=O.[NH2:27][C:28]([NH2:30])=[O:29].Cl>CCO>[O:29]=[C:28]1[NH:30][CH:16]([C:18]2[CH:26]=[CH:25][C:21]([C:22]([OH:24])=[O:23])=[CH:20][CH:19]=2)[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 120884-Formylbenzoic acid

Product 1

HCID 51348810HCID 51348810, compoundYield 2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of 1,2-diphenylethanone (392 mg, 2.0 mmol), 4-formylbenzoic acid (274 mg, 1.8 mmol) and urea (324 mg, 5.4 mmol) in EtOH (40 mL) was added concentrated HCl (0.17 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 inverse-phase column to afford Compound 90 as a tan powder (11 mg, 2%). 1H NMR (MeOH-d4 500 MHz TMS): δ 7.99 (d, J=7.0 Hz, 2H), 7.47 (d, J=7.0 Hz, 2H), 7.25 (s, 5H), 7.03 (s, 3H), 6.85 (s, 2H), 5.40 (s, 1H); MS (ESI): m/z 371.0 [M+1]+.

Workup

  1. customThe volatiles were removed under reduced pressure
  2. customPurification by inverse-phase column

Sources & evidence

ORD record
ord-f6968d08267c479eafc642d50689f271
Source dataset
uspto-grants-2014_06
Patent number
US08741915B2

Reaction notes

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