Water → HCID 21876424, compound

HRID 1454665Notes

Reaction equation

HRID 1454665 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][NH:18][C:19](=[O:27])OC3C=CC=CC=3)=[CH:12][CH:11]=2)[C:3]=1[N+:28]([O-:30])=[O:29].[CH3:31][C:32]1[CH:33]=[CH:34][C:35]([S:38]([NH2:41])(=[O:40])=[O:39])=[CH:36][CH:37]=1.[H-].[Na+].O>CN(C=O)C>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][NH:18][C:19]([NH:41][S:38]([C:35]3[CH:36]=[CH:37][C:32]([CH3:31])=[CH:33][CH:34]=3)(=[O:39])=[O:40])=[O:27])=[CH:12][CH:11]=2)[C:3]=1[N+:28]([O-:30])=[O:29]

Participants

6

Reactant 4

HCID 962WaterHCID 6269P-ToluenesulfonamideHCID 24758Sodium hydrideHCID 21875604Phenyl 2-{4-[(4,6-dimethyl-3-nitro-2-pyridinyl)amino]phenyl}ethylcarbamate

Product 1

HCID 21876424HCID 21876424, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of phenyl 2-{4-[(4,6-dimethyl-3-nitro-2-pyridinyl)amino]phenyl}ethylcarbamate (step 2, 10.0 g, 24.6 mmol) and p-toluenesulfonamide (6.3 g, 36.8 mmol) in DMF (100 mL) was added sodium hydride (2.0 g, 50 mmol). The reaction mixture was stirred at room temperature for 1 h. The reaction mixture was poured into water (300 mL) and extracted with ethyl acetate/toluene (v/v, 2:1, 2×300 mL). The organic extracts were washed with water (100 mL) and brine (200 mL), then dried (Na2SO4). Removal of the solvent gave crude product. Recrystallization from ethyl acetate gave 9.6 g (81%) of the title compound as brown solids. The mother liquor was concentrated and the residue was purified by flash column chromatography on silica gel eluting with hexane/ethyl acetate (1:1) to afford 1.9 g (16%) of the title compound as brown solids.

Workup

  1. extractionextracted with ethyl acetate/toluene (v/v, 2:1, 2×300 mL)
  2. washThe organic extracts were washed with water (100 mL) and brine (200 mL)
  3. dry with materialdried (Na2SO4)
  4. customRemoval of the solvent
  5. customgave crude product
  6. customRecrystallization from ethyl acetate

Sources & evidence

ORD record
ord-0bd71aa80b584900a7553cb1ade79926
Source dataset
uspto-grants-2009_01
Patent number
US07479564B2

Reaction notes

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