Hydrochloric Acid → 4-Iodo-2,6-dimethylaniline hydrochloride

HRID 270739Notes

Reaction equation

HRID 270739 reaction equation
C(=O)(O)[O-].[Na+].[CH3:6][C:7]1[CH:13]=[CH:12][CH:11]=[C:10]([CH3:14])[C:8]=1[NH2:9].[I:15][Cl:16].Cl>CO>[ClH:16].[I:15][C:12]1[CH:11]=[C:10]([CH3:14])[C:8]([NH2:9])=[C:7]([CH3:6])[CH:13]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 68962,6-DimethylanilineHCID 24640Iodine chlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 573482104-Iodo-2,6-dimethylaniline hydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of sodium bicarbonate (126 g, 1500 mmol) and 2,6-dimethylaniline (61.5 mL, 500 mmol) in methanol (700 mL) was added iodine monochloride (1.0 M in dichloromethane, 550 mL, 550 mmol) at room temperature over 1 h. After addition was complete, stirring was continued for 3 h. The reaction was filtered to remove excess sodium bicarbonate and the solvent removed in vacuo. The residue was redissolved in diethyl ether (1.5 L) and treated with hydrochloric acid (2M in ether, 375 mL, 750 mmol). The resulting suspension was stored in the freezer (−15° C.) overnight. The solid was filtered and washed with diethyl ether until it became colorless to give 126.5 g (89%) as a grey-green powder. 1H-NMR (DMSO-d6) δ 2.33 (s, 6H), 7.48 (s, 2H), 9.05 (bs, 3H); 13C-NMR (DMSO-d6) δ 17.4, 91.5, 133.1, 131.2, 136.9.

Workup

  1. additionAfter addition
  2. filtrationThe reaction was filtered
  3. customto remove excess sodium bicarbonate
  4. customthe solvent removed in vacuo
  5. dissolutionThe residue was redissolved in diethyl ether (1.5 L)
  6. customwas stored in the freezer (−15° C.) overnight
  7. filtrationThe solid was filtered
  8. washwashed with diethyl ether until it
  9. customto give 126.5 g (89%) as a grey-green powder

Sources & evidence

ORD record
ord-d454fe3234c8403a9e6b8eeeb6cedcd9
Source dataset
uspto-grants-2008_11
Patent number
US07449586B2

Reaction notes

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