Sodium Hydroxide → HCID 460660, compound

HRID 327176Notes

Reaction equation

HRID 327176 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[CH:14]=2)(=[O:12])=[O:11])=[CH:6][CH:5]=1)([O-])=O.[OH-].[Na+]>C(O)C>[CH3:19][C:15]1[CH:14]=[C:13]([S:10]([C:7]2[CH:6]=[CH:5][C:4]([NH2:1])=[CH:9][CH:8]=2)(=[O:12])=[O:11])[CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 21480110HCID 21480110, compound

Product 1

HCID 460660HCID 460660, compoundYield 101.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred solution of 3-methylphenyl 4-nitrophenyl sulfone (0.50 g, 1.8 mmol) and stannous chloride dehydrate (2.03 g, 9.0 mmol) in absolute ethanol (5 mL) was heated at reflux for 1 hour. The reaction mixture was poured into ice water and the aqueous solution basified with 15% NaOH and extracted with ethyl acetate (2×100 mL). The combined organic extracts were dried (MgSO4), filtered, and the solvent removed in vacuo to yield an off-white solid. Recrystallization from absolute ethanol/hexane yielded the title benzenamine (0.45 g, 100%) as a white solid; mp 183°-185° C. 1H--NMR (300 MHz, d6 --DMSO): 2.36 (s, 3H, CH 3), 6.17 (s, 2H, NH2), 6.61 (dd, 2H, J=7.0, 1.8 Hz, aromatic), 7.43 (d, 2H, J=7.1 Hz, aromatic), 7.54 (d, 2H, J=8.7 Hz, aromatic), 7.63 (m, 2H, aromatic). MS (CI, CH4): 248(M+1).

Workup

  1. temperatureat reflux for 1 hour
  2. extractionextracted with ethyl acetate (2×100 mL)
  3. dry with materialThe combined organic extracts were dried (MgSO4)
  4. filtrationfiltered
  5. customthe solvent removed in vacuo
  6. customto yield an off-white solid
  7. customRecrystallization from absolute ethanol/hexane

Sources & evidence

ORD record
ord-4f1b22056e2c4cae920a1f56d7c6046b
Source dataset
uspto-grants-1993_12
Patent number
US05272163

Reaction notes

Loading…