1-methyl-1H-imidazole-4-sulfonyl chloride → HCID 16045836, compound

HRID 655630Notes

Reaction equation

HRID 655630 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][C:4]=1[NH:11][C:12]1[C:21]([NH2:22])=[N:20][C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13]=1.[CH3:23][N:24]1[CH:28]=[C:27]([S:29](Cl)(=[O:31])=[O:30])[N:26]=[CH:25]1>N1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][C:4]=1[NH:11][C:12]1[C:21]([NH:22][S:29]([C:27]2[N:26]=[CH:25][N:24]([CH3:23])[CH:28]=2)(=[O:31])=[O:30])=[N:20][C:19]2[C:14]([N:13]=1)=[CH:15][CH:16]=[CH:17][CH:18]=2

Participants

4

Reactant 2

HCID 27368871-methyl-1H-imidazole-4-sulfonyl chlorideHCID 16045757HCID 16045757, compound

Product 1

HCID 16045836HCID 16045836, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

N-(2,5-dimethoxyphenyl)quinoxaline-2,3-diamine (50 mg, 0.17 mmol), 1-methylimidazole-4-sulfonylchloride (91.4 mg, 0.51 mmol, commercially available from Acros) are dissolved in pyridine (0.3 ml) and the reaction mixture was stirred at rt, overnight. When TLC confirms the total consumption of N-(2,5-dimethoxyphenyl)quinoxaline-2,3-diamine, the product is extracted with CHCl3. The organic layer is washed with water, 1.5N HCl and brine then dried over Na2SO4. The solvent is removed under reduced pressure and the residue obtained is purified by recrystallization from MeOH to afford 47 mg (64%) of the title compound as a yellow solid. HPLC (max plot) 95%, rt. 3.91 min. LC/MS: (ES+): 441.2.

Workup

  1. customthe total consumption of N-(2,5-dimethoxyphenyl)quinoxaline-2,3-diamine
  2. extractionthe product is extracted with CHCl3
  3. washThe organic layer is washed with water, 1.5N HCl and brine
  4. dry with materialthen dried over Na2SO4
  5. customThe solvent is removed under reduced pressure
  6. customthe residue obtained
  7. customis purified by recrystallization from MeOH

Sources & evidence

ORD record
ord-13af82d02f3e486dace35a1fa834fa50
Source dataset
uspto-grants-2011_12
Patent number
US08071597B2

Reaction notes

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