Acetonitrile → N-(3-((2-chloro-5-methoxyphenyl)amino)quinoxalin-2-yl)-3-nitrobenzenesulfonamide

HRID 1050935Notes

Reaction equation

HRID 1050935 reaction equation
Cl.[Cl:2][C:3]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:4]=1[NH2:5].C(#N)C.C1CCN2C(=NCCC2)CC1.Cl[C:27]1[C:28]([NH:37][S:38]([C:41]2[CH:46]=[CH:45][CH:44]=[C:43]([N+:47]([O-:49])=[O:48])[CH:42]=2)(=[O:40])=[O:39])=[N:29][C:30]2[C:35]([N:36]=1)=[CH:34][CH:33]=[CH:32][CH:31]=2>CO>[Cl:2][C:3]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:4]=1[NH:5][C:27]1[C:28]([NH:37][S:38]([C:41]2[CH:46]=[CH:45][CH:44]=[C:43]([N+:47]([O-:49])=[O:48])[CH:42]=2)(=[O:39])=[O:40])=[N:29][C:30]2[C:35]([N:36]=1)=[CH:34][CH:33]=[CH:32][CH:31]=2

Participants

6

Reactant 4

HCID 6342Acetonitrile3×HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 27239002-Chloro-5-methoxyanilinium chlorideHCID 5007601N-(3-chloroquinoxalin-2-yl)-3-nitrobenzenesulfonamide

Product 1

HCID 57448456N-(3-((2-chloro-5-methoxyphenyl)amino)quinoxalin-2-yl)-3-nitrobenzenesulfonamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
20 °C

Procedure

Prepare a solution with 0.585 kg of 2-chloro-5-methoxyaniline-HCl, 3.5 volumes of acetonitrile and 0.46 kg of DBU. (solution A) Mix 1 kg of N-(3-chloroquinoxalin-2-yl)-3-nitrobenzenesulfonamide and 5.5 volumes of acetonitrile. Heat to reflux. Add solution A and 1 volume of acetonitrile onto the reaction mixture. After completion of the reaction at reflux, cool down at 20° C., dilute with 10 volumes of methanol and filter. Wash the cake 3 times with 5 volumes of methanol and dry it under vacuum.

Workup

  1. temperatureHeat to reflux
  2. customAfter completion of the reaction
  3. temperatureat reflux
  4. filtrationfilter
  5. washWash the cake 3 times with 5 volumes of methanol
  6. customdry it under vacuum

Sources & evidence

ORD record
ord-72ae39d2c6da44d48c250df8ea1cc4da
Source dataset
uspto-grants-2016_07
Patent number
US09388143B2

Reaction notes

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