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

HRID 537859Notes

Reaction equation

HRID 537859 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-423d51e7448945089c95e95deb1d6229
Source dataset
uspto-grants-2014_10
Patent number
US08865709B2

Reaction notes

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