Hydrochloric Acid → HCID 66826446, compound

HRID 2177967Notes

Reaction equation

HRID 2177967 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=O)[CH:5]=[CH:6][CH:7]=1.[CH2:17]([O:19][C:20]1[CH:21]=[C:22]([CH:25]=[C:26]([N+:29]([O-:31])=[O:30])[C:27]=1[OH:28])[CH:23]=O)[CH3:18].[NH2:32][C:33]([NH2:35])=[O:34].Cl>C(O)C>[CH2:17]([O:19][C:20]1[CH:21]=[C:22]([CH:23]2[C:8]([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=3)=[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[NH:35][C:33](=[O:34])[NH:32]2)[CH:25]=[C:26]([N+:29]([O-:31])=[O:30])[C:27]=1[OH:28])[CH3:18]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1176UreaHCID 5848783-Ethoxy-4-hydroxy-5-nitrobenzaldehydeHCID 27590612-(3-fluorophenyl)-1-phenylethanone

Product 1

HCID 66826446HCID 66826446, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-(3-fluorophenyl)-1-phenylethanone (commercially available) (200 mg, 0.93 mmol), 3-ethoxy-4-hydroxy-5-nitrobenzaldehyde (197 mg, 0.93 mmol), urea (168 mg, 2.8 mmol), conc. hydrochloric acid (0.5 mL) in ethanol (3 mL) was refluxed for 61 hours. After cooling to room temperature, the mixture was evaporated and purified by silica gel column chromatography (petroleum ether/ethyl acetate=3:1) to give Compound 115 (85.8 mg, yield 20%). HNMR (DMSO-d6 400 MHZ): δ 10.31 (brs, 1H), 8.82 (s, 1H), 7.59 (s, 1H), 7.45 (d, J=1.2 Hz, 1H), 7.31-7.22 (m, 6H), 7.10-7.00 (m, 1H), 6.84-6.80 (m, 1H), 6.64-6.56 (m, 2H), 5.26 (d, J=2.4 Hz, 1H), 4.15-4.00 (m, 2H), 1.36 (t, J=6.8 Hz, 3H). MS (ESI): m/z 450.0 [M+H]+.

Workup

  1. temperaturewas refluxed for 61 hours
  2. customthe mixture was evaporated
  3. custompurified by silica gel column chromatography (petroleum ether/ethyl acetate=3:1)

Sources & evidence

ORD record
ord-0f5cc555864a45e8b3b707a1c8d964c9
Source dataset
uspto-grants-2015_06
Patent number
US09067893B2

Reaction notes

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