Ethanol → HCID 10801498, compound

HRID 327159Notes

Reaction equation

HRID 327159 reaction equation
COC1C=CC=CC=1[C:9]1[CH:14]=[C:13]([N+]([O-])=O)[CH:12]=[CH:11][C:10]=1[S:18]([C:21]1[CH:26]=[CH:25][C:24]([N+:27]([O-])=O)=[CH:23][C:22]=1C1C=CC=CC=1OC)(=[O:20])=[O:19].[OH-].[Na+].[CH2:40]([OH:42])C>>[CH3:40][O:42][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[S:18]([C:21]1[CH:22]=[CH:23][C:24]([NH2:27])=[CH:25][CH:26]=1)(=[O:19])=[O:20]

Participants

4

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 53982667HCID 53982667, compound

Product 1

HCID 10801498HCID 10801498, compoundYield 49%

Conditions

Temperature
50 °C

Procedure

To a stirred slurry of 2-methoxyphenyl-4-nitrophenyl sulfone (12.36 g, 4.2 mmol) and 90 mL of absolute ethanol was added stannous chloride dehydrate (47.4 g, 21 mmol) in one portion. The mixture was heated to 50° C. where an exothermic reaction caused the solution to strongly reflux. The mixture was allowed to stir at ambient temperature for 30 min., poured onto ice-water and made strongly basic by the addition of 350 mL of 15% NaOH. The mixture was extracted with methylene chloride (3×275 mL, the extracts dried (MgSO4), filtered, and the solvent removed in vacuo to yield a white solid which was recrystallized from ethyl acetate-hexane. After cooling the solid was filtered to yield the title benzenamine (5.38 g, 49%) as a white solid; mp 206°-208° C. 1H--NMR (300 MHz, d6 --DMSO): 3.75 (s, 3H, OCH3), 6.10 (s, 2H, NH2), 6.56-6.61 (m, 2H, aromatic), 7.07-7.13 (m, 2H, aromatic), 7.49-7.61 (m, 3H, aromatic), 7.90 (dd, 1H, J=8.1 & 1.7 Hz, aromatic). MS (CI, CH4): 264 (M+1).

Workup

  1. customan exothermic reaction
  2. temperatureto strongly reflux
  3. additionpoured onto ice-water
  4. extractionThe mixture was extracted with methylene chloride (3×275 mL
  5. dry with materialthe extracts dried (MgSO4)
  6. filtrationfiltered
  7. customthe solvent removed in vacuo
  8. customto yield a white solid which
  9. customwas recrystallized from ethyl acetate-hexane
  10. temperatureAfter cooling the solid
  11. filtrationwas filtered

Sources & evidence

ORD record
ord-66adfb0544614630add935d10f255b85
Source dataset
uspto-grants-1993_12
Patent number
US05272163

Reaction notes

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