Hydrochloric Acid → HCID 66825853, compound

HRID 924865Notes

Reaction equation

HRID 924865 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): δ10.25 (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-db98caa457db488395e213b84b982511
Source dataset
uspto-grants-2016_03
Patent number
US09283229B2

Reaction notes

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