Water → HCID 13799845, compound

HRID 1906493Notes

Reaction equation

HRID 1906493 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[NH:12][CH:13]=[CH:14][C:15]=2[C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].[H-].[Na+].[C:25]1(C)[C:26]([S:31](Cl)(=[O:33])=[O:32])=[CH:27][CH:28]=[CH:29][CH:30]=1.O.[CH3:37]N(C=O)C>>[C:29]1([CH3:37])[CH:30]=[CH:25][C:26]([S:31]([N:12]2[CH:13]=[CH:14][C:15]([C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)=[C:11]2[C:8]2[CH:7]=[CH:6][C:5]([S:2]([CH3:1])(=[O:3])=[O:4])=[CH:10][CH:9]=2)(=[O:32])=[O:33])=[CH:27][CH:28]=1

Participants

6

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 8623o-Toluenesulfonyl chlorideHCID 24758Sodium hydrideHCID 10313600HCID 10313600, compound

Product 1

HCID 13799845HCID 13799845, compoundYield 100%

Procedure

A solution of 2-(4-methylsulfonylphenyl)-3-(4-fluorophenyl)-1H-pyrrole (31.6 g, 0.1 mole) in 200 ml dry N,N'-dimethylformamide was cooled in an ice bath and treated with sodium hydride (2.4 g, 0.1 mole). The mixture was stirred for one hour and reacted with toluenesulfonyl chloride (19.0 g, 0.1 mole). The mixture was stirred at room temperature and poured into one liter of cold water with vigorous stirring. The resulting precipitate was collected by filtration, washed with water and dried. The off white solid was triturated with 150 ml chloroform, washed with other and dried. The product was collected in 100% yield (46.9 g); m.p. 228.5°-229°.

Workup

  1. stirringThe mixture was stirred at room temperature
  2. filtrationThe resulting precipitate was collected by filtration
  3. washwashed with water
  4. customdried
  5. customThe off white solid was triturated with 150 ml chloroform
  6. washwashed with other and
  7. customdried
  8. customThe product was collected in 100% yield (46.9 g)

Sources & evidence

ORD record
ord-b222a52be87d4a43bdf04d251f66f00a
Source dataset
uspto-grants-1987_03
Patent number
US04652582

Reaction notes

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