HCID 19877037, compound → HCID 89815347, compound

HRID 1051826Notes

Reaction equation

HRID 1051826 reaction equation
[NH2:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[C:4]([S:13][CH3:14])[CH:3]=1.[I:15]Cl.CC(O)=O>C(O)(=O)C.CCOC(C)=O>[NH2:1][C:2]1[C:12]([I:15])=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[C:4]([S:13][CH3:14])[CH:3]=1

Participants

5

Reactant 2

HCID 19877037HCID 19877037, compoundHCID 89814802HCID 89814802, compound

Product 1

HCID 89815347HCID 89815347, compoundYield 62.4%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To a pre-heated, 60° C. solution of ethyl 4-amino-2-(methylthio)benzoate (65 mmol) in acetic acid (150 mL) was added ICl/AcOH solution (1M, 72 mL, 72 mmol) dropwise during 40 min and the temperature was maintained at 60° C. for 3 h. After cooling to rt the reaction was diluted with EtOAc (500 mL), washed with 5% Na2S2O3 solution (3×100 mL) and brine (200 mL), dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The crude product was purified by silica gel chromatography (0-20% EtOAc/Hexanes) afford ethyl 4-amino-5-iodo-2-(methylthio)benzoate (13.67 g, 53% yield).

Workup

  1. temperatureAfter cooling to rt the reaction
  2. washwashed with 5% Na2S2O3 solution (3×100 mL) and brine (200 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by silica gel chromatography (0-20% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-908f3fbe65974d839f7b43f2067dd3bb
Source dataset
uspto-grants-2016_07
Patent number
US09388190B2

Reaction notes

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