2-Nitrobenzenesulfonyl chloride → HCID 86690003, compound

HRID 1186732Notes

Reaction equation

HRID 1186732 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([N:8]2[C:17]3[CH:16]=[CH:15][C:14]4[CH2:18][CH2:19][CH2:20][CH2:21][C:13]=4[C:12]=3[NH:11][C:10](=[O:22])[C:9]2=[O:23])[CH:5]=[CH:6][CH:7]=1.[N+:24]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[S:33](Cl)(=[O:35])=[O:34])([O-:26])=[O:25]>N1C=CC=CC=1>[O:22]=[C:10]1[NH:11][C:12]2[C:13]3[CH2:21][CH2:20][CH2:19][CH2:18][C:14]=3[CH:15]=[CH:16][C:17]=2[N:8]([C:4]2[CH:3]=[C:2]([NH:1][S:33]([C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=3[N+:24]([O-:26])=[O:25])(=[O:34])=[O:35])[CH:7]=[CH:6][CH:5]=2)[C:9]1=[O:23]

Participants

4

Reactant 2

HCID 155402-Nitrobenzenesulfonyl chlorideHCID 56640367HCID 56640367, compound

Product 1

HCID 86690003HCID 86690003, compoundYield 100.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 4-(3-aminophenyl)-1,4,7,8,9,10-hexahydrobenzo[f]quinoxaline-2,3-dione (228 mg, 0.74 mmol), 2-nitrobenzenesulfonyl chloride (247 mg, 1.11 mmol), and dry pyridine (5 mL) was refluxed at 80° C. for 4 hours. After cooling on standing, the solvent was removed by evaporation under reduced pressure. The obtained residue was extracted with chloroform, washed with water and a dilute hydrochloric acid aqueous solution, and dried over anhydrous sodium sulfate. The solvent was removed by evaporation under reduced pressure. The obtained residue was purified by silica gel column chromatography (chloroform/methanol=100/1) to obtain the titled compound as a brown crystal (365 mg, yield 100%).

Workup

  1. temperatureAfter cooling
  2. customthe solvent was removed by evaporation under reduced pressure
  3. extractionThe obtained residue was extracted with chloroform
  4. washwashed with water
  5. dry with materiala dilute hydrochloric acid aqueous solution, and dried over anhydrous sodium sulfate
  6. customThe solvent was removed by evaporation under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography (chloroform/methanol=100/1)

Sources & evidence

ORD record
ord-524986d34aae438b99939d2246180d7a
Source dataset
uspto-grants-2014_03
Patent number
US08673915B2

Reaction notes

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