Pyridine → N-(3-Aminophenyl)-1-phenylmethanesulfonamide

HRID 1038425Notes

Reaction equation

HRID 1038425 reaction equation
[C:1]1([NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1N.[N:9]1C=CC=CC=1.[C:15]1([CH2:21][S:22](Cl)(=[O:24])=[O:23])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>CC#N>[NH2:9][C:5]1[CH:6]=[C:1]([NH:8][S:22]([CH2:21][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)(=[O:24])=[O:23])[CH:2]=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 7243O-PhenylenediamineHCID 74740Phenylmethanesulfonyl chloride

Product 1

HCID 16772451N-(3-Aminophenyl)-1-phenylmethanesulfonamideYield 36.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of phenylenediamine (6.93 g, 64.08 mmol) in CH3CN was added pyridine (6.05 g, 76.89 mmol). After stirring at room temperature for 10 minutes it was cooled to ˜10° C. and added phenylmethylsulfonyl chloride (6 g, 32.04 mmol). Reaction was further stirred for 14 hours at ambient temperature. Reaction was quenched with aqueous NaHCO3 (saturated) and stirred for 30 minutes. Solid was filtered, and dried under high vacuum to obtain crude N-(3-aminophenyl)-1-phenylmethanesulfonamide 26 (3.1 g, 19% yield). MS (ES) m/z 263 (M+H+).

Workup

  1. temperaturewas cooled to ˜10° C.
  2. customReaction
  3. stirringwas further stirred for 14 hours at ambient temperature
  4. customReaction
  5. customwas quenched with aqueous NaHCO3 (saturated)
  6. stirringstirred for 30 minutes
  7. filtrationSolid was filtered
  8. customdried under high vacuum

Sources & evidence

ORD record
ord-a3b1811b7bdb4bfe8b0fedb5dbbee769
Source dataset
uspto-grants-2013_10
Patent number
US08551992B2

Reaction notes

Loading…