Benzenamine, 3,5-bis(trifluoromethyl)- → HCID 86658340, compound

HRID 2198036Notes

Reaction equation

HRID 2198036 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][S:5](Cl)(=[O:7])=[O:6].[F:9][C:10]([F:23])([F:22])[C:11]1[CH:12]=[C:13]([CH:15]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:17]=1)[NH2:14]>N1C=CC=CC=1>[F:9][C:10]([F:22])([F:23])[C:11]1[CH:12]=[C:13]([NH:14][S:5]([CH2:4][CH2:3][CH2:2][Cl:1])(=[O:7])=[O:6])[CH:15]=[C:16]([C:18]([F:19])([F:21])[F:20])[CH:17]=1

Participants

4

Reactant 2

HCID 9480Benzenamine, 3,5-bis(trifluoromethyl)-HCID 154103-Chloropropanesulphonyl chloride

Product 1

HCID 86658340HCID 86658340, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 3-chloropropanesulfonyl chloride (5.0 g) and 3,5-bis(trifluoromethyl)aniline (6.47 g) in pyridine (50 ml) was stirred at room temperature for 16 hr. The reaction solution was concentrated under reduced pressure, and the residue was partitioned between ethyl acetate and 1N hydrochloric acid. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate 95:5-60:40) to give the title compound (7.20 g, yield 69%) as a pale-brown solid.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. customthe residue was partitioned between ethyl acetate and 1N hydrochloric acid
  3. washThe organic layer was washed with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customthe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate 95:5-60:40)

Sources & evidence

ORD record
ord-b2e80c91a7dd49728830476d2005bca0
Source dataset
uspto-grants-2012_12
Patent number
US08338622B2

Reaction notes

Loading…