Hydrochloric Acid → N-(3-chloroquinoxalin-2-yl)-3-nitrobenzenesulfonamide

HRID 2201397Notes

Reaction equation

HRID 2201397 reaction equation
Cl[C:2]1[C:11]([Cl:12])=[N:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[N+:13]([C:16]1[CH:17]=[C:18]([S:22]([NH2:25])(=[O:24])=[O:23])[CH:19]=[CH:20][CH:21]=1)([O-:15])=[O:14].C1CCN2C(=NCCC2)CC1.Cl>CO.C(#N)C>[Cl:12][C:11]1[C:2]([NH:25][S:22]([C:18]2[CH:19]=[CH:20][CH:21]=[C:16]([N+:13]([O-:15])=[O:14])[CH:17]=2)(=[O:24])=[O:23])=[N:3][C:4]2[C:9]([N:10]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 166592,3-DichloroquinoxalineHCID 67138Benzenesulfonamide, 3-nitro-HCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene

Product 1

HCID 5007601N-(3-chloroquinoxalin-2-yl)-3-nitrobenzenesulfonamide

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent2×

Conditions

Temperature
5 °C

Procedure

1 kg of 2,3 dichloroquinoxaline and 1 kg of 3-nitrobenzenesulfonamide are mixed in 5 volumes of acetonitrile. The reaction mixture is heated to reflux. 2.3 kg of DBU and 1 volume of acetonitrile are added. After completion of the reaction, cool down at 5° C. Add 12 volumes of methanol and 1.53 kg of HCl, filter the reaction mixture. Wash the cake with 6 volumes of methanol and dry under vacuum.

Workup

  1. temperatureThe reaction mixture is heated to reflux
  2. customAfter completion of the reaction
  3. filtrationfilter the reaction mixture
  4. washWash the cake with 6 volumes of methanol
  5. customdry under vacuum

Sources & evidence

ORD record
ord-d7a87ec68b324d1fbeb566400d40011a
Source dataset
uspto-grants-2016_06
Patent number
US09364475B2

Reaction notes

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