Stannous chloride dihydrate → 5-Amino-2-iodobenzamide

HRID 503687Notes

Reaction equation

HRID 503687 reaction equation
O.O.[Sn](Cl)Cl.[I:6][C:7]1[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[CH:12][C:8]=1[C:9]([NH2:11])=[O:10]>CN(C=O)C>[NH2:16][C:13]1[CH:14]=[CH:15][C:7]([I:6])=[C:8]([CH:12]=1)[C:9]([NH2:11])=[O:10]

Participants

4

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 98039472-Iodo-5-nitrobenzamide

Product 1

HCID 155476225-Amino-2-iodobenzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

15.1 g (67 mmol) of tin(II) chloride dihydrate are added to a solution of 4.9 g (16.8 mmol) of the compound from Example 3A in 200 ml of DMF. The reaction mixture is stirred at 50° C. for one hour, and then the DMF is removed in vacuo. The residue is partitioned between 1 l of ethyl acetate and water, the phases are separated, and the organic phase is discarded. The aqueous phase is basified with 10% strength sodium hydroxide solution and again extracted with 500 ml of ethyl acetate. The product is dried over magnesium sulfate, filtered with suction and concentrated in vacuo. 3.95 g (90% of theory) of the title compound are obtained and are reacted without further purification in the next stage.

Workup

  1. customthe DMF is removed in vacuo
  2. customThe residue is partitioned between 1 l of ethyl acetate and water
  3. customthe phases are separated
  4. extractionagain extracted with 500 ml of ethyl acetate
  5. dry with materialThe product is dried over magnesium sulfate
  6. filtrationfiltered with suction
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-47fbc14711a846ac98ef725b6cda40b4
Source dataset
uspto-grants-2010_08
Patent number
US07776922B2

Reaction notes

Loading…