Thiophenol → HCID 58909955, compound

HRID 1296032Notes

Reaction equation

HRID 1296032 reaction equation
C1(S)C=CC=CC=1.[H-].[Na+].[CH3:10][NH:11][C:12](=[O:55])[C:13]1[CH:18]=[C:17]([Br:19])[C:16]([CH2:20][N:21]([CH2:34][C:35]([C:37]2[CH:42]=[C:41]([C:43]([CH3:46])([CH3:45])[CH3:44])[C:40]([OH:47])=[C:39]([C:48]([CH3:51])([CH3:50])[CH3:49])[CH:38]=2)=[O:36])S(C2C=CC([N+]([O-])=O)=CC=2)(=O)=O)=[CH:15][C:14]=1[O:52][CH2:53][CH3:54]>CN(C)C=O.C(OCC)(=O)C>[CH3:10][NH:11][C:12](=[O:55])[C:13]1[CH:18]=[C:17]([Br:19])[C:16]([CH2:20][NH:21][CH2:34][C:35]([C:37]2[CH:38]=[C:39]([C:48]([CH3:51])([CH3:50])[CH3:49])[C:40]([OH:47])=[C:41]([C:43]([CH3:46])([CH3:45])[CH3:44])[CH:42]=2)=[O:36])=[CH:15][C:14]=1[O:52][CH2:53][CH3:54]

Participants

6

Reactant 3

HCID 7969ThiophenolHCID 24758Sodium hydrideHCID 58909999HCID 58909999, compound

Product 1

HCID 58909955HCID 58909955, compoundYield 79.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

After dissolving thiophenol (1.27 ml) in dimethylformamide (20 ml), sodium hydride (480 mg) was added. The mixture was stirred at room temperature for 30 minutes and then the N1-methyl-5-bromo-4-({{2-[3,5-di(tert-butyl)-4-hydroxyphenyl]-2-oxoethyl}[(4-nitrophenyl)sulfonyl]amino}methyl)-2-ethoxybenzamide (2.95 g) was added. After stirring at room temperature for 1 hour, the mixture was diluted with ethyl acetate and washed with water and brine, and then the organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated and the residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate) to yield the title compound (1.75 g) as a light orange oil. (78% yield)

Workup

  1. additionwas added
  2. stirringAfter stirring at room temperature for 1 hour
  3. washwashed with water and brine
  4. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customthe residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate)

Sources & evidence

ORD record
ord-39311be382bd4ec5a97c30deece596d0
Source dataset
uspto-grants-2007_07
Patent number
US07244730B2

Reaction notes

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