Hydrochloric Acid → HCID 51348946, compound

HRID 401070Notes

Reaction equation

HRID 401070 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.[OH:16][C:17]1[CH:24]=[CH:23][C:20]([CH:21]=O)=[CH:19][C:18]=1[N+:25]([O-:27])=[O:26].[NH2:28][C:29]([NH2:31])=[O:30].Cl>CCO>[OH:16][C:17]1[CH:24]=[CH:23][C:20]([CH:21]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:19][C:18]=1[N+:25]([O-:27])=[O:26]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1176UreaHCID 99482-PhenylacetophenoneHCID 181694-Hydroxy-3-nitrobenzaldehyde

Product 1

HCID 51348946HCID 51348946, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of 1,2-diphenylethanone (704 mg, 3.59 mmol), 4-hydroxy-3-nitrobenzaldehyde (500 mg, 2.99 mmol) and urea (538 mg, 8.97 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 workup procedure was followed. Purification by silica gel column chromatography (PE:EA=1:1) gave Compound 95 as an off-white power (102 mg, 9%). 1H NMR (DMSO-d6 500 MHz TMS): δ 10.09 (s, 1H), 8.69 (s, 1H), 7.82 (d, J=2.0 Hz, 1H), 7.52-7.57 (m, 2H), 7.21-7.26 (m, 5H), 7.13 (d, J=10.5 Hz, 1H), 7.01 (t, J=27.5 Hz, 3H), 7.81 (d, J=8.5 Hz, 2H), 5.26 (d, J=3.5 Hz, 1H); MS (ESI): m/z 388.1 [M+1]+

Workup

  1. customThe volatiles were removed under reduced pressure and standard aqueous workup procedure
  2. customPurification by silica gel column chromatography (PE:EA=1:1)

Sources & evidence

ORD record
ord-4e017d454b86425cb58b8b9ddb53af2d
Source dataset
uspto-grants-2014_06
Patent number
US08741915B2

Reaction notes

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