4-Aminophenol → 4-Chloro-N-[3-(4-hydroxy-phenylamino)-quinoxalin-2-yl]-benzenesulfonamide

HRID 44207Notes

Reaction equation

HRID 44207 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([S:16]([NH:19][C:20]2[C:29](Cl)=[N:28][C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[N:21]=2)(=[O:18])=[O:17])=[CH:12][CH:11]=1>>[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([S:16]([NH:19][C:20]2[C:29]([NH:1][C:2]3[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=3)=[N:28][C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[N:21]=2)(=[O:17])=[O:18])=[CH:12][CH:11]=1

Participants

3

Reactant 2

HCID 4034-AminophenolHCID 23665104-Chloro-N-(3-chloro-quinoxalin-2-yl)-benzenesulfonamide

Product 1

HCID 15671984-Chloro-N-[3-(4-hydroxy-phenylamino)-quinoxalin-2-yl]-benzenesulfonamideYield 60%

Procedure

A solution of 4-aminophenol (22 mg, 0.2 mmol) in xylenes (2 mL), was treated with 4-chloro-N-(3-chloro-quinoxalin-2-yl)-benzenesulfonamide (35.4 mg, 0.1 mmol) in one portion. The reaction mixture was heated under reflux in an inert atmosphere of nitrogen for 25 h. Reaction progress was monitored by TLC. Upon completion of the reaction, the mixture was cooled, which resulted in compound 5-4 precipitating from the solution as red-yellow crystals. The crystals were filtered and washed with hot methanol (5 mL) and pentane (5×5 mL). Yield 60%, mp=298-301° C. TLC Rf=0.35 (hexanes/EtOAc 1:1). 1H NMR (DMSO-d6, 600 MHz): δ 6.75 (d, J=8.4 Hz, 2H), 7.30 (t, J=7.2 Hz, 1H), 7.35 (t, J=7.2 Hz, 1H), 7.66 (d, J=8.4 Hz, 2H), 7.69 (d, J=7.8 Hz, 2H), 7.89 (br.s, 1H), 8.11 (d, J=7.8 Hz, 2H), 8.81 (br.s, 1H), 9.30 (br.s, 1H), 12.29 (br.s, 1H). HPLC/MS: [M+H]+ m/z 426. HRMS: Calcd. [M+H]+ m/z 427.0632, Observed 427.0644.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux in an inert atmosphere of nitrogen for 25 h
  3. customReaction progress
  4. customUpon completion of the reaction
  5. temperaturethe mixture was cooled

Sources & evidence

ORD record
ord-3bddd3ab236746fc93f5dc7e62ec0822
Source dataset
uspto-grants-2013_09
Patent number
US08541415B2

Reaction notes

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