Hydrochloric Acid → HCID 66825853, compound

HRID 401078Notes

Reaction equation

HRID 401078 reaction equation
[C:1]1([CH2:7][C:8]([C:10]2[CH:14]=[CH:13][N:12]([S:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)(=[O:17])=[O:16])[CH:11]=2)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:24]([O:26][C:27]1[CH:28]=[C:29]([CH:32]=[C:33]([N+:36]([O-:38])=[O:37])[C:34]=1[OH:35])[CH:30]=O)[CH3:25].[NH2:39][C:40]([NH2:42])=[O:41].Cl>C(O)C>[CH2:24]([O:26][C:27]1[CH:28]=[C:29]([CH:30]2[C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[C:8]([C:10]3[CH:14]=[CH:13][N:12]([S:15]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)(=[O:17])=[O:16])[CH:11]=3)[NH:42][C:40](=[O:41])[NH:39]2)[CH:32]=[C:33]([N+:36]([O-:38])=[O:37])[C:34]=1[OH:35])[CH3:25]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1176UreaHCID 5848783-Ethoxy-4-hydroxy-5-nitrobenzaldehydeHCID 21802476HCID 21802476, compound2×

Product 1

HCID 66825853HCID 66825853, compoundYield 28.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-phenyl-1-(1-(phenylsulfonyl)-1H-pyrrol-3-yl)ethanone (Intermediate 52) (200 mg, 0.6 mmol), 3-ethoxy-4-hydroxy-5-nitrobenzaldehyde (130 mg, 0.6 mmol), and urea (108 mg, 1.8 mmol) in 10 mL of ethanol was added 0.2 mL of concentrated HCl solution. The mixture refluxed overnight, concentrated in vacuo, and purified by TLC (PE: EtOAc=1:2) to afford the Compound 107 (95 mg, yield 27.6%). 1H NMR (DMSO-d6 400 MHz): δ 10.25 (s, 1H), 8.53 (s, 1H), 7.86 (d, J=7.6 Hz, 2H), 7.77 (t, J=7.6 Hz, 1H), 7.65 (t, J=8.0 Hz, 2H), 7.49 (s, 1H), 7.36 (s, 1H), 7.31 (d, J=2.0 Hz, 1H), 7.17-7.14 (m, 3H), 7.12 (t, J=2.8 Hz, 1H), 7.00 (d, J=2.0 Hz, 1H), 6.91-6.89 (m, 2H), 5.70 (m, 1H), 5.10 (d, J=2.4 Hz, 1H), 4.05-3.90 (m, 2H), 1.29 (t, J=7.2 Hz, 3H); MS (ESI): m/z 561.3 [M+1]+.

Workup

  1. temperatureThe mixture refluxed overnight
  2. concentrationconcentrated in vacuo
  3. custompurified by TLC (PE: EtOAc=1:2)

Sources & evidence

ORD record
ord-0cec74463a2843c0955cfc2b1c26510a
Source dataset
uspto-grants-2014_06
Patent number
US08741915B2

Reaction notes

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