Sulfuryl chloride → HCID 86620783, compound

HRID 554329Notes

Reaction equation

HRID 554329 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[NH:12][CH:11]=[C:10]([CH:13]=[O:14])[CH:9]=1.[H-].[Na+].C1O[CH2:30][CH2:29]OCCOCCOCCOC1.[S:32](Cl)(Cl)(=[O:34])=[O:33]>O1CCCC1.[Cl-].[Na+].O>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:12]([S:32]([C:30]2[CH:29]=[CH:3][CH:8]=[CH:9][C:10]=2[C:11]#[N:12])(=[O:34])=[O:33])[CH:11]=[C:10]([CH:13]=[O:14])[CH:9]=1

Participants

7

Reactant 4

HCID 24648Sulfuryl chlorideHCID 24758Sodium hydrideHCID 3633615-Crown-5HCID 469085935-(2-Fluorophenyl)-1H-pyrrole-3-carboxaldehyde

Product 1

HCID 86620783HCID 86620783, compoundYield 154.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution (28 mL) of 5-(2-fluorophenyl)-1H-pyrrole-3-carbaldehyde (284 mg) in tetrahydrofuran was added sodium hydride (60% in oil, 181 mg) at room temperature and the mixture was stirred for 30 min. 15-Crown-5 (992 mg) was added dropwise and the mixture was stirred for 30 min, (2-cyanobenzene) sulfonyl chloride (606 mg) was added, and the mixture was further stirred for 1 hr. Saturated brine was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=4:1→2:3) to give the title compound as colorless crystals (yield 410 mg, 77%).

Workup

  1. stirringthe mixture was stirred for 30 min
  2. stirringthe mixture was further stirred for 1 hr
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=4:1→2:3)

Sources & evidence

ORD record
ord-78126406371a4941939007f11e4c8a3c
Source dataset
uspto-grants-2011_11
Patent number
US08048909B2

Reaction notes

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