Methanesulfonyl chloride → HCID 1485426, compound

HRID 2045924Notes

Reaction equation

HRID 2045924 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=[CH:3][C:2]=1[C:11]1[CH:12]=[C:13]([NH2:17])[CH:14]=[CH:15][CH:16]=1.[CH3:18][S:19](Cl)(=[O:21])=[O:20]>N1C=CC=CC=1.O>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=[CH:3][C:2]=1[C:11]1[CH:12]=[C:13]([NH:17][S:19]([CH3:18])(=[O:21])=[O:20])[CH:14]=[CH:15][CH:16]=1

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 8072643-(2-quinoxalinyl)aniline

Product 1

HCID 1485426HCID 1485426, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

To a solution of (3-quinoxalin-2-ylphenyl)amine (2.21 g, 0.01 mol) in pyridine (10 mL), methanesulfonyl chloride (0.77 mL, 0.01 mol) was added dropwise at 0-5° C. with stirring. The reaction mixture was stirred overnight at room temperature, and then diluted with water. The resulting solid was filtered and dried to afford N-[3-(quinoxalin-2-yl)phenyl]methanesulfonamide (2.6 g, 87% yield). LCMS calculated for C15H13N3O2S (M+H): 300.07. found 300. 1H-NMR (DMSO-d6, 250 Mhz) δH: 10.01 (1H, br. s), 9.50 (1H, s), 8.20-8.00 (4H, m), 7.95-7.70 (2H, m), 7.60-7.52 (1H, m), 7.48-7.40 (1H, m), 3.04 (3H, s).

Workup

  1. stirringThe reaction mixture was stirred overnight at room temperature
  2. filtrationThe resulting solid was filtered
  3. customdried

Sources & evidence

ORD record
ord-2c9db0a8abab4d998cbdf307d4045d7d
Source dataset
uspto-grants-2013_11
Patent number
US08592415B2

Reaction notes

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