Thionyl Chloride → 2,6-Difluoro-3-(propane-1-sulfonylamino)-benzoyl chloride

HRID 1261001Notes

Reaction equation

HRID 1261001 reaction equation
[F:1][C:2]1[C:10]([NH:11][S:12]([CH2:15][CH2:16][CH3:17])(=[O:14])=[O:13])=[CH:9][CH:8]=[C:7]([F:18])[C:3]=1[C:4](O)=[O:5].S(Cl)([Cl:21])=O>C1(C)C=CC=CC=1>[F:1][C:2]1[C:10]([NH:11][S:12]([CH2:15][CH2:16][CH3:17])(=[O:14])=[O:13])=[CH:9][CH:8]=[C:7]([F:18])[C:3]=1[C:4]([Cl:21])=[O:5]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 461929232,6-Difluoro-3-[(propylsulfonyl)amino]benzoic acid

Product 1

HCID 580868612,6-Difluoro-3-(propane-1-sulfonylamino)-benzoyl chloride

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To 2,6-difluoro-3-(propane-1-sulfonylamino)-benzoic acid (45, 1.50 g, 5.4 mmol) was added toluene (7.0 mL) and thionyl chloride (15.0 mL, 0.21 mmol). The reaction was heated to reflux for 3 hours. The reaction was concentrated to give crude compound that was used in the next step.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 3 hours
  3. concentrationThe reaction was concentrated
  4. customto give crude compound that

Sources & evidence

ORD record
ord-b97ae7024ca84e2ba0b2aee5012605a3
Source dataset
uspto-grants-2013_06
Patent number
US08470818B2

Reaction notes

Loading…