Sodium hydride → HCID 15029355, compound

HRID 1707561Notes

Reaction equation

HRID 1707561 reaction equation
[H-].[Na+].[CH:3]([C:6]1([CH3:22])[C:10](=[O:11])[NH:9][C:8]([C:12]2[CH:21]=[CH:20][CH:19]=[CH:18][C:13]=2[C:14]([O:16][CH3:17])=[O:15])=[N:7]1)([CH3:5])[CH3:4].[N+:23]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[S:32](Cl)=O)([O-:25])=[O:24]>O1CCCC1>[CH:3]([C:6]1([CH3:22])[C:10](=[O:11])[N:9]([S:32][C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=2[N+:23]([O-:25])=[O:24])[C:8]([C:12]2[CH:21]=[CH:20][CH:19]=[CH:18][C:13]=2[C:14]([O:16][CH3:17])=[O:15])=[N:7]1)([CH3:5])[CH3:4]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 97942682-Nitrobenzenesulfinyl chlorideHCID 12764366HCID 12764366, compound

Product 1

HCID 15029355HCID 15029355, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A slurry of sodium hydride (0.76 g, 0.019 mol, 60% in mineral oil) and tetrahydrofuran is added dropwise to a 0° C. solution of methyl o-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)benzoate (5.0 g, 0.018 mol) and tetrahydrofuran under a nitrogen atmosphere. After stirring for 1 hour at room temperature, 2-nitrobenzenesulfinyl chloride (3.8 g, 0.020 mol) is added dropwise to the mixture and stirring is continued at room temperature for 72 hours. The reaction mixture is filtered and the filtrate is concentrated in vacuo to give a yellow solid. The solid is chromatographed using silica gel and 10% ethyl acetate in methylene chloride as eluent to yield the title compound as a pale yellow solid (1.08 g, 14%, mp 143°-148° C., identified by IR and NMR spectral analyses.

Workup

  1. stirringstirring
  2. waitis continued at room temperature for 72 hours
  3. filtrationThe reaction mixture is filtered
  4. concentrationthe filtrate is concentrated in vacuo
  5. customto give a yellow solid
  6. customThe solid is chromatographed

Sources & evidence

ORD record
ord-9b7396aead9c4c15904cb6e2c203ebd9
Source dataset
uspto-grants-1994_10
Patent number
US05354727

Reaction notes

Loading…