O-Toluidine → HCID 178424352, compound

HRID 1079445Notes

Reaction equation

HRID 1079445 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 2.5 N 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-248b5c8aee7d45e7adfcd3b20f417f24
Source dataset
uspto-grants-1996_12
Patent number
US05580892

Reaction notes

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