Calcium Carbonate → Benzoic acid, 4-amino-2-chloro-5-iodo-, methyl ester

HRID 1976778Notes

Reaction equation

HRID 1976778 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([Cl:12])[CH:3]=1.C(=O)([O-])[O-].[Ca+2].[I:18](Cl)(=O)=O.I(Cl)(=O)=O.C([N+](C)(C)C)C1C=CC=CC=1>ClCCl.CO>[NH2:1][C:2]1[C:11]([I:18])=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([Cl:12])[CH:3]=1

Participants

6

Reactant 3

HCID 10112Calcium CarbonateHCID 11839197Methyl 4-Amino-2-chlorobenzoateHCID 56924451Trimethylbenzylammonium Dichloroiodate2×

Product 1

HCID 11839203Benzoic acid, 4-amino-2-chloro-5-iodo-, methyl ester

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of methyl 4-amino-2-chloro-benzoate (1.14 g, 6.16 mmol) in dichloromethane (30 mL) and methanol (15 mL) was treated sequentially with calcium carbonate (1.85 g, 18.5 mmol) and benzyl trimethylammonium dichloroiodate (3.22 g, 9.24 mmol), stirred for 18 hours, treated with additional benzyl trimethylammonium dichloroiodate (2 g, 5.75 mmol), stirred for 3 days, filtered into a separatory funnel, washed with saturated NaHSO3, dried (MgSO4), filtered, and concentrated. The concentrate was recrystallized from ethyl acetate to provide the majority of the desired product. The filtrate was concentrated, and the concentrate was purified on silica gel with a gradient of from 10% to 20% ethyl acetate/hexanes to provide a total of 1.3 g of the desired product.

Workup

  1. stirringstirred for 3 days
  2. filtrationfiltered into a separatory funnel
  3. washwashed with saturated NaHSO3
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe concentrate was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-364e510a725b4430a20e8ffb8c85b244
Source dataset
uspto-grants-2001_05
Patent number
US06228868B1

Reaction notes

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