N,N-Dimethylaniline → N-(4-Amino-3-nitro-phenyl)-4-isopropyl-benzenesulfonamide

HRID 450723

Reaction equation

HRID 450723 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([NH2:10])[CH:7]=[CH:6][C:5]=1[NH2:11])([O-:3])=[O:2].CN(C)C1C=CC=CC=1.[CH:21]([C:24]1[CH:29]=[CH:28][C:27]([S:30](Cl)(=[O:32])=[O:31])=[CH:26][CH:25]=1)([CH3:23])[CH3:22]>C(#N)C>[NH2:11][C:5]1[CH:6]=[CH:7][C:8]([NH:10][S:30]([C:27]2[CH:28]=[CH:29][C:24]([CH:21]([CH3:23])[CH3:22])=[CH:25][CH:26]=2)(=[O:32])=[O:31])=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 949N,N-DimethylanilineHCID 27348824-(Propan-2-yl)benzene-1-sulfonyl chlorideHCID 43383702-Nitro-4-phenylenediamine

Product 1

HCID 27993411N-(4-Amino-3-nitro-phenyl)-4-isopropyl-benzenesulfonamideYield 55.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of 2-nitro-benzene-1,4-diamine (10 g, 65.30 mmol) and N,N-dimethylaniline (8.7 g, 71.83 mmol) in acetonitrile (310 ml) at 0° C. 4-isopropyl-benzenesulfonylchloride (13.85 g, 63.34 mmol) was added over a period of 1 h. The mixture was stirred at 0° C. for 1 h and for 16 h at room temperature. After concentrating the mixture in vacuo the obtained oil was triturated with water. The precipitate was collected, washed with ethanol and dried in vacuo to give the product as a yellow powder (11.76 g, 54%).

Workup

  1. concentrationAfter concentrating the mixture in vacuo the obtained oil
  2. customwas triturated with water
  3. customThe precipitate was collected
  4. washwashed with ethanol
  5. customdried in vacuo

Sources & evidence

ORD record
ord-d1517fabb6114385b7dc8398287ec5a8
Source dataset
uspto-grants-2013_07
Patent number
US08486984B2

Linked notes

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