Hydrochloric Acid → HCID 68622036, compound

HRID 16130Notes

Reaction equation

HRID 16130 reaction equation
S(=O)(=O)(O)O.[CH3:6][C:7]1[CH:8]=[C:9]([CH:13]=[CH:14][CH:15]=1)[N:10]([CH3:12])[CH3:11].[N:16]([O-])=O.[Na+].[ClH:20]>C(OCC)C.[Fe].O>[ClH:20].[ClH:20].[CH3:6][C:7]1[C:8]([NH2:16])=[C:9]([N:10]([CH3:12])[CH3:11])[CH:13]=[CH:14][CH:15]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 1118Sulfuric AcidHCID 8488N,N-dimethyl-m-toluidineHCID 23668193Sodium Nitrite

Product 1

HCID 68622036HCID 68622036, compoundYield 60%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

To a 250 cm3 round bottom flask was added water (100 cm3) and the temperature was reduced to 5° C. with an ice bath. To this cooled solution was carefully added sulphuric acid (98%, 22.5 g). To this solution was added 3-methyl-N,N-dimethylaniline (10 g, 74 mmol) and then sodium nitrite (5.6 g, 81.4 mmol), and the solution was stirred at room temperature for 1 hour. Iron (Fe) filings (12.8 g, 229 mmol) were added and the mixture stirred for a further 2 hours. The solution was filtered and then neutralized with saturated sodium hydrogen carbonate solution and the organics were extracted into ethyl acetate (3×100 cm3). The extracts were dried over magnesium sulphate, filtered, and concentrated to give a brown oil. The oil was dissolved in diethyl ether (100 cm3) and concentrated hydrochloric acid (50 cm3) was added. The solution was evaporated to dryness to give the title compound (10 g, 60%) as a light tan solid. νmax (KBr)/cm−1: 2849 (CH), 2821 (CH), 2543 (CH), 2444 (CH), 1586 (C═N), 1487 (CH), 1445 (CH), 1415 (CH), 1138 (CH); dH (250 MHz; D2O): 7.59 (1H, s, ArH), 7.50 (2H, s, ArH), 3.24 (6H, s, CH3), 2.39 (3H, s, CH3); δC (62.9 MHz; D2O) 18.9 (CH3), 48.8 (CH3), 122.1 (ArC), 126.2 (ArC), 127.6 (ArC), 133.7 (ArC), 137.4 (ArC), 144.4 (ArC).

Workup

  1. customthe temperature was reduced to 5° C. with an ice bath
  2. filtrationThe solution was filtered
  3. extractionthe organics were extracted into ethyl acetate (3×100 cm3)
  4. dry with materialThe extracts were dried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a brown oil
  8. customThe solution was evaporated to dryness

Sources & evidence

ORD record
ord-adbce445510545508697905720bc62fc
Source dataset
uspto-grants-2010_06
Patent number
US07737138B2

Reaction notes

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