4-Fluoroaniline → HCID 1400613, compound

HRID 237369Notes

Reaction equation

HRID 237369 reaction equation
Cl[C:2]1[C:3]([NH:12][S:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)(=[O:15])=[O:14])=[N:4][C:5]2[C:10]([N:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[F:22][C:23]1[CH:29]=[CH:28][C:26]([NH2:27])=[CH:25][CH:24]=1.CC(N(C)C)=O>CO>[F:22][C:23]1[CH:29]=[CH:28][C:26]([NH:27][C:2]2[C:3]([NH:12][S:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)(=[O:15])=[O:14])=[N:4][C:5]3[C:10]([N:11]=2)=[CH:9][CH:8]=[CH:7][CH:6]=3)=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 97314-FluoroanilineHCID 31374DimethylacetamideHCID 698553HCID 698553, compound

Product 1

HCID 1400613HCID 1400613, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
120 °C

Procedure

A CEM microwave reaction vessel was charged with N-(3-chloroquinoxalin-2-yl)benzenesulfonamide (52 mg, 0.16 mmol), 4-fluoroaniline (36 mg, 0.32 mmol), and 0.8 mL of dimethylacetamide. The vessel was sealed and the reaction mixture was heated under microwave radiation for 25 m at 120° C. in a CEM Discover microwave instrument. Methanol (1 mL) was added to the reaction mixture and after 20 minutes the product precipitated out of the solution. Filtration yielded 39 mg (62%) of N-(3-(4-fluorophenylamino)quinoxalin-2-yl)benzenesulfonamide. 1H-NMR (400 MHz, d6-DMSO): δ 12.30 (s, 1H), 9.11 (s, 1H), 8.16-8.10 (d, 2H), 8.02-7.90 (m, 3H), 7.68-7.58 (m, 3H), 7.55-7.51 (m, 1H), 7.41-7.32 (m, 2H), 7.25-7.16 (m, 2H); MS (EI) C20H15FN4O2S: 395.0 (MH+).

Workup

  1. customA CEM microwave reaction vessel
  2. customThe vessel was sealed
  3. customprecipitated out of the solution
  4. filtrationFiltration

Sources & evidence

ORD record
ord-02267284eb464e9095eb1ceac07578b6
Source dataset
uspto-grants-2014_02
Patent number
US08642584B2

Reaction notes

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