Acetyl chloride → HCID 13799846, compound

HRID 1906494Notes

Reaction equation

HRID 1906494 reaction equation
[H-].[Na+].[CH3:3][S:4]([C:7]1[CH:12]=[CH:11][C:10]([C:13]2[NH:14][CH:15]=[CH:16][C:17]=2[C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)=[CH:9][CH:8]=1)(=[O:6])=[O:5].[C:25](Cl)(=[O:27])[CH3:26]>CN(C=O)C>[C:25]([N:14]1[CH:15]=[CH:16][C:17]([C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)=[C:13]1[C:10]1[CH:9]=[CH:8][C:7]([S:4]([CH3:3])(=[O:5])=[O:6])=[CH:12][CH:11]=1)(=[O:27])[CH3:26]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 24758Sodium hydrideHCID 10313600HCID 10313600, compound

Product 1

HCID 13799846HCID 13799846, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A suspension of sodium hydride (2.64 g, 0.11 mole) in 100 ml dry N,N'-dimethylformamide was heated dropwise with a solution of 2-(4-methylsulfonylphenyl)-3-(4-fluorophenyl)-1H-pyrrole (31.56 g, 0.1 mole) in 200 ml dry N,N'-dimethylformamide and stirred for one hour at room temperature. The mixture was then treated dropwise with acetyl chloride (7.9 g, 0.1 mole). The mixture was stirred for three hours and concentrated in vacuo. The residue was triturated with water, collected by filtration, dried, and column chromatographed on silica gel with toluene-ethyl acetate (3:2) as the mobile phase. The product was collected in 25% yield; m.p. 211°-214°.

Workup

  1. stirringThe mixture was stirred for three hours
  2. concentrationconcentrated in vacuo
  3. customThe residue was triturated with water
  4. filtrationcollected by filtration
  5. customdried
  6. customcolumn chromatographed on silica gel with toluene-ethyl acetate (3:2) as the mobile phase
  7. customThe product was collected in 25% yield

Sources & evidence

ORD record
ord-45dcfac3b4b74ae0ac4f7fd7bcbceaa3
Source dataset
uspto-grants-1987_03
Patent number
US04652582

Reaction notes

Loading…