4-Toluenesulfonyl chloride → N-(4-Methoxy-2-nitrophenyl)-4-methylbenzenesulfonamide

HRID 1493316Notes

Reaction equation

HRID 1493316 reaction equation
[CH3:1][O:2][C:3]1[CH:9]=[CH:8][C:6]([NH2:7])=[C:5]([N+:10]([O-:12])=[O:11])[CH:4]=1.[S:13](Cl)([C:16]1[CH:22]=[CH:21][C:19]([CH3:20])=[CH:18][CH:17]=1)(=[O:15])=[O:14]>N1C=CC=CC=1>[CH:3]([O:2][CH:22]([CH3:21])[CH3:16])([CH3:9])[CH3:4].[CH3:20][C:19]1[CH:21]=[CH:22][C:16]([S:13]([NH:7][C:6]2[CH:8]=[CH:9][C:3]([O:2][CH3:1])=[CH:4][C:5]=2[N+:10]([O-:12])=[O:11])(=[O:15])=[O:14])=[CH:17][CH:18]=1

Participants

5

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 667934-Methoxy-2-nitroaniline

Product 2

HCID 7914Diisopropyl EtherHCID 225676N-(4-Methoxy-2-nitrophenyl)-4-methylbenzenesulfonamideYield 151.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

50 g of 4-methoxy-2-nitroaniline are stirred at 0° C. in 300 ml of pyridine. 56.7 g of tosyl chloride are added in portions at 0° C. and the mixture is then stirred for two hours at room temperature, left to stand overnight and poured into an ice/water mixture. The crystals obtained are filtered off and washed with water and then with isopropyl ether to give 72.8 g of 2-(4-methylbenzenesulfonylamino)-5-methoxynitrobenzene in the form of crystals melting at 99° C.

Workup

  1. waitleft
  2. waitto stand overnight
  3. customThe crystals obtained
  4. filtrationare filtered off
  5. washwashed with water

Sources & evidence

ORD record
ord-2c77ab02eec44adab3efec4aa987a25d
Source dataset
uspto-grants-1991_06
Patent number
US05021443

Reaction notes

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