Benzenesulfonyl chloride → 5-fluoro-2,4-bis[(N-benzenesulfonyl)amino]toluene

HRID 1077375Notes

Reaction equation

HRID 1077375 reaction equation
[F:1][C:2]1[C:3]([NH2:10])=[CH:4][C:5]([NH2:9])=[C:6]([CH3:8])[CH:7]=1.[C:11]1([S:17](Cl)(=[O:19])=[O:18])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>N1C=CC=CC=1>[F:1][C:2]1[C:3]([NH:10][S:17]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)(=[O:19])=[O:18])=[CH:4][C:5]([NH:9][S:17]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)(=[O:19])=[O:18])=[C:6]([CH3:8])[CH:7]=1

Participants

4

Reactant 2

HCID 7369Benzenesulfonyl chlorideHCID 178215114-Fluoro-6-methylbenzene-1,3-diamine

Product 1

HCID 194311615-fluoro-2,4-bis[(N-benzenesulfonyl)amino]tolueneYield 41%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
120 °C

Procedure

8 g 5-fluoro-2,4-diaminotoluene from Step 2 are dissolved in 250 ml pyridine, mixed with 7.9 ml benzenesulfonyl chloride, and stirred for 1 hour at 120° C. After cooling, the reaction preparation is poured over ice. The obtained precipitate is washed with water, dried in vacuum over phosphorus pentoxide, and recrystallized from methanol. 3.9 g (41% of theory) 5-fluoro-2,4-bis[(N-benzenesulfonyl)amino]toluene are obtained which melts at 146° C.

Workup

  1. temperatureAfter cooling
  2. customthe reaction preparation
  3. additionis poured over ice
  4. washThe obtained precipitate is washed with water
  5. dry with materialdried in vacuum over phosphorus pentoxide
  6. customrecrystallized from methanol

Sources & evidence

ORD record
ord-252434250f0648a3995f280cae4f6906
Source dataset
uspto-grants-1996_08
Patent number
US05542953

Reaction notes

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