O-Toluidine → HCID 178424352, compound

HRID 725906Notes

Reaction equation

HRID 725906 reaction equation
[NH2:1][C:2]1[C:3]([CH3:8])=[CH:4][CH:5]=[CH:6][CH:7]=1.[NH:9]1[CH2:13][CH2:12][N:11]=[C:10]1S(O)(=O)=O.[OH-].[Na+]>CC#N>[CH3:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[N:1]=[C:10]1[NH:11][CH2:12][CH2:13][NH:9]1

Participants

5

Reactant 3

HCID 7242O-ToluidineHCID 14798Sodium HydroxideHCID 2745614,5-dihydro-1H-imidazole-2-sulfonic acid2×

Product 1

HCID 178424352HCID 178424352, compoundYield 5.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Ortho toluidine (536 mg, 531 μl, 5 mmol) and imidazoline-2-sulfonic acid (750 mg, 5 mmol, (Compound 7 obtained as described above)) and CH3CN (6ml) were heated in a thick-walled glass tube at 150° C. for 16 hours. The reaction mixture was then cooled to 0° and made basic to pH 14 by addition of 2.5N NaOH solution. The mixture was extracted with methylene chloride, the combine extracts were died (K2CO3) and evaporated to dryness. Flash chromatography on silica gel yielded the title compound as a tan colored solid (47.0 mg, 5.37%).

Workup

  1. temperatureThe reaction mixture was then cooled to 0°
  2. extractionThe mixture was extracted with methylene chloride
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-ea23f05e3ac145ed84d90fd4465ebdbb
Source dataset
uspto-grants-1998_01
Patent number
US05708015

Reaction notes

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