2-Nitropropane → HCID 13160142, compound

HRID 2412382Notes

Reaction equation

HRID 2412382 reaction equation
[O-:1][CH2:2][CH3:3].[Na+].[N+](C(C)C)([O-])=O.ClC[C:13]1[CH:18]=[CH:17][CH:16]=C[C:14]=1[S:19]([NH:22][C:23]([NH:25][C:26]1[N:31]=[C:30]([CH3:32])[CH:29]=[C:28]([CH3:33])[N:27]=1)=[O:24])(=[O:21])=[O:20]>C(O)C>[CH:2]([C:3]1[CH:16]=[CH:17][CH:18]=[CH:13][C:14]=1[S:19]([NH:22][C:23]([NH:25][C:26]1[N:27]=[C:28]([CH3:33])[CH:29]=[C:30]([CH3:32])[N:31]=1)=[O:24])(=[O:21])=[O:20])=[O:1]

Participants

5

Reactant 3

HCID 3982-NitropropaneHCID 2723922Sodium ethoxideHCID 13160141HCID 13160141, compound

Product 1

HCID 13160142HCID 13160142, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of 6.26 mmol of sodium ethoxide in 10 ml of absolute ethanol under an argon atmosphere was added 0.80 ml of 2-nitropropane. Next 0.74 g (2.09 mmol) of 2-chloromethyl-N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]benzenesulfonamide was added and the solution was heated to reflux. The mixture became pasty shortly after heating was begun and an additional 3 ml of ethanol was added to facilitate stirring. After heating for 4 hours, the solvent was removed under reduced pressure and the residue was dissolved in 12 ml of water. The crude product was precipitated by neutralization of the solution with 3N hydrochloric acid. The crude product was purified by preparative thin layer chromatography on silica gel and subsequent recrystallization from acetone to provide the title compound, m.p. 157° C. (decomp.). The infrared spectrum showed a new carbonyl band at 1675 cm-1, indicative of the formation of an aldehyde, in addition to the urea carbonyl band at 1710 cm-1. The nuclear magnetic resonance spectrum showed peaks at 10.57 ppm and 10.67 ppm which are consistent with an aromatic aldehyde with restricted rotation.

Workup

  1. temperaturethe solution was heated to reflux
  2. temperatureafter heating
  3. temperatureAfter heating for 4 hours
  4. customthe solvent was removed under reduced pressure
  5. dissolutionthe residue was dissolved in 12 ml of water
  6. customThe crude product was precipitated by neutralization of the solution with 3N hydrochloric acid
  7. customThe crude product was purified by preparative thin layer chromatography on silica gel and subsequent recrystallization from acetone

Sources & evidence

ORD record
ord-ddce85d282624050babb19e3e843528a
Source dataset
uspto-grants-1985_01
Patent number
US04492599

Reaction notes

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