Calcium Carbonate → 7-Iodo-1,3-benzodioxol-4-amine

HRID 1785084Notes

Reaction equation

HRID 1785084 reaction equation
I(Cl)(=O)=O.[I:5](Cl)(=O)=O.C([N+](C)(C)C)C1C=CC=CC=1.[O:20]1[C:24]2[CH:25]=[CH:26][CH:27]=[C:28]([NH2:29])[C:23]=2[O:22][CH2:21]1.C(=O)([O-])[O-].[Ca+2]>CO.ClCCl.O>[I:5][C:25]1[C:24]2[O:20][CH2:21][O:22][C:23]=2[C:28]([NH2:29])=[CH:27][CH:26]=1

Participants

7

Reactant 3

HCID 10112Calcium CarbonateHCID 103131651,3-Benzodioxol-4-amineHCID 56924451Trimethylbenzylammonium Dichloroiodate

Product 1

HCID 226627507-Iodo-1,3-benzodioxol-4-amine

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Benzyltrimethylammonium dichloroiodate (2.8 g) was added portionwise over 10 minutes to a stirred mixture of 1,3-benzodioxol-4-amine (1 g), calcium carbonate (0.95 g) in methanol (5 ml) and dichloromethane (10 ml). The reaction mixture was stirred at ambient temperature for 1.5 hours. The reaction mixture was diluted with water and extracted with dichloromethane. The organics were washed with water saturated brine and dried over magnesium sulfate. The residue was purified by column chromatography on silica using a gradient of an 8:1 mixture of dichloromethane/isohexane to Dichloromethane as eluent. There was thus obtained 7-iodo-1,3-benzodioxol-4-amine as a beige crystalline solid (1.1 g); NMR Spectrum: (DMSOd6) 5.04 (bs, 2H); 5.94 (s, 2H); 6.13 (d, 1H), 6.80 (d, 1H).

Workup

  1. extractionextracted with dichloromethane
  2. washThe organics were washed with water saturated brine
  3. dry with materialdried over magnesium sulfate
  4. customThe residue was purified by column chromatography on silica using
  5. additiona gradient of an 8:1 mixture of dichloromethane/isohexane to Dichloromethane as eluent

Sources & evidence

ORD record
ord-689ca49645354ed7b4eb7185c06147f4
Source dataset
uspto-grants-2009_03
Patent number
US07504408B2

Reaction notes

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