Calcium Carbonate → HCID 57421915, compound

HRID 735325Notes

Reaction equation

HRID 735325 reaction equation
[I:1]Cl.[C:3]1([S:9]([C:12]2[CH:17]=[CH:16][C:15]([NH2:18])=[CH:14][CH:13]=2)(=[O:11])=[O:10])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(=O)([O-])[O-].[Ca+2]>CO>[I:1][C:14]1[CH:13]=[C:12]([S:9]([C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)(=[O:10])=[O:11])[CH:17]=[CH:16][C:15]=1[NH2:18]

Participants

5

Reactant 3

HCID 10112Calcium CarbonateHCID 24640Iodine chlorideHCID 5166664-(Phenylsulfonyl)aniline

Product 1

HCID 57421915HCID 57421915, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Iodine chloride (1.94 g, 12 mmol) in methanol (30 mL) was added to a mixture of [4-(phenylsulfonyl)phenyl]amine (Step 1, 2.33 g, 10 mmol) and calcium carbonate (2.0 g, 20 mmol) in methanol (20 mL). The reaction was stirred at room temperature for 72 hours. The reaction mixture was filtered and the filtrate evaporated. The residue was taken up in ethyl acetate and washed with sodium sulfite solution and brine, then evaporated. The residue was triturated with diethyl ether to give [2-iodo-4-(phenylsulfonyl)phenyl]amine (2.3 g). 1H NMR (400 MHz, d6-DMSO) δ 7.99 (1H, d, J=2.1 Hz), 7.87-7.85 (2H, m), 7.64-7.54 (4H, m), 6.77 (1H, d, J=8.6 Hz), 6.24 (2H, s).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe filtrate evaporated
  3. washwashed with sodium sulfite solution and brine
  4. customevaporated
  5. customThe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-d650a143dac64fa9b0308775a6a568d3
Source dataset
uspto-grants-2009_09
Patent number
US07592456B2

Reaction notes

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