2-(Phenylmethanesulfinyl)aniline → HCID 13672816, compound

HRID 1732012Notes

Reaction equation

HRID 1732012 reaction equation
[CH2:1]([S:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1N)=[O:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N([O-])=O.[Na+]>OS(O)(=O)=O.O>[CH:14]1[C:15]2[C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[CH2:1][S:8](=[O:9])[C:10]=2[CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 2

HCID 136728152-(Phenylmethanesulfinyl)anilineHCID 23668193Sodium Nitrite

Product 1

HCID 13672816HCID 13672816, compoundYield 72.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 1118Sulfuric AcidSolvent

Procedure

To a stirred suspension of benzyl-(2-aminophenyl)-sulfoxide (1.9 g; 0.008 mol) in 30 ml of 11% H2SO4 was added a solution of sodium nitrite (0.78 g; 0.011 mol) in 20 ml of water at about 0° C. After 1 hour at 0° C. to the yellow solution was quickly added a solution of cupric nitrate trihydrate (34.2 g; 0.140 mol) in 75 ml of water and cuprous oxide (1.33 g; 0.009 mol). The solution was allowed to warm to room temperature and stirred for further 5 hours. The solid was filtered and treated with hot ethyl acetate. The solution was dried over sodium sulfate concentrated and the residue was crystallized from ethyl acetate/pentane (1:4) to give 6H-dibenzo[b,d]thiopyran-5-oxide (1.25 g; yield 71%); m.p. 97°-100° C. By proceeding analogously the following compounds were obtained:

Workup

  1. filtrationThe solid was filtered
  2. additiontreated with hot ethyl acetate
  3. dry with materialThe solution was dried over sodium sulfate
  4. concentrationconcentrated
  5. customthe residue was crystallized from ethyl acetate/pentane (1:4)

Sources & evidence

ORD record
ord-23bb45b8257f4da68003739bb160d46e
Source dataset
uspto-grants-1986_11
Patent number
US04624949

Reaction notes

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