Dimethylformamide → 4-(4-Fluorophenoxy)benzenesulphonyl chloride

HRID 1953229Notes

Reaction equation

HRID 1953229 reaction equation
[F:1][C:2]1[CH:18]=[CH:17][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([S:13](O)(=[O:15])=[O:14])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.[Na].S(Cl)([Cl:22])=O.CN(C)C=O>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:18]=[CH:17][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([S:13]([Cl:22])(=[O:15])=[O:14])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 5360545SodiumHCID 110225964-(4-fluorophenoxy)benzenesulfonic Acid

Product 1

HCID 27827574-(4-Fluorophenoxy)benzenesulphonyl chloride

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a slurry of 15.0 g (0.052 mol) of 4-(4-fluorophenoxy)benzenesulfonic acid□, sodium salt, in 150 mL of dry toluene was added 11.3 mL (0.155 mol, 3 equivalents) of thionyl chloride and 0.04 mL (0.5 mmol, 0.01 equivalents) of dimethylformamide. The resulting mixture was stirred at room temperature for 48 hours, filtered through diatomaceous earth, and concentrated under reduced pressure to 40 mL. This solution was used without further purification to prepare 1-[4-(4-fluorophenoxy)benzenesulfonylamino] cyclopentanecarboxylic acid benzyl ester.

Workup

  1. filtrationfiltered through diatomaceous earth
  2. concentrationconcentrated under reduced pressure to 40 mL
  3. customThis solution was used without further purification
  4. customto prepare 1-[4-(4-fluorophenoxy)benzenesulfonylamino] cyclopentanecarboxylic acid benzyl ester

Sources & evidence

ORD record
ord-e2518a412ec54e5b887d14cd5fbbcffd
Source dataset
uspto-grants-2000_09
Patent number
US06114568

Reaction notes

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