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

HRID 447235Notes

Reaction equation

HRID 447235 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, 1.5 moles) and 2,6-dimethylaniline (61.5 mL, 500 mmoles) in methanol (700 mL) was added iodine monochloride (1.0 M in dichloromethane, 550 mL, 550 mmoles) 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 re-dissolved in diethyl ether (1.5 L) and treated with hydrochloric acid (2M in ether, 375 mL, 750 mmoles). 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 re-dissolved 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-9d8440480efa4499af1eec4c3b933fbc
Source dataset
uspto-grants-2013_07
Patent number
US08481546B2

Reaction notes

Loading…