1,5-Diiodopentane → HCID 59570142, compound

HRID 2071135Notes

Reaction equation

HRID 2071135 reaction equation
I[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]I.[NH2:8][C:9]1[CH:10]=[C:11]([C:19]([O:21][CH3:22])=[O:20])[CH:12]=[C:13]([CH:18]=1)[C:14]([O:16][CH3:17])=[O:15]>CN(C1C=CN=CC=1)C.O>[N:8]1([C:9]2[CH:18]=[C:13]([C:14]([O:16][CH3:17])=[O:15])[CH:12]=[C:11]([CH:10]=2)[C:19]([O:21][CH3:22])=[O:20])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 123541,5-DiiodopentaneHCID 66831Dimethyl 5-aminoisophthalate

Product 1

HCID 59570142HCID 59570142, compoundYield 33%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolvent

Procedure

1,5-diiodopentane (0.85 ml, 1.8 g, 5.74 mmol, 3 eq) was added to a stirred solution of dimethyl 5-aminoisophthalate (0.40 g, 1.91 mmol, 1 eq) and DMAP (0.467 g, 3.82 mmol, 2.1 eq) at 100° C. under Ar. After heating overnight the reaction was cooled to room temperature and poured in water. The mixture was extracted with EtOAc (×2). The combined organic extracts were washed with water (×4), brine (×1), and dried over Na2SO4. The inorganics were filtered off, and the solvent was removed in vacuo. Purification via flash chromatography yielded 0.1736 g, 0.626 mmol, 33% yield) of the product.

Workup

  1. temperatureAfter heating overnight the reaction
  2. extractionThe mixture was extracted with EtOAc (×2)
  3. washThe combined organic extracts were washed with water (×4), brine (×1)
  4. dry with materialdried over Na2SO4
  5. filtrationThe inorganics were filtered off
  6. customthe solvent was removed in vacuo
  7. customPurification via flash chromatography
  8. customyielded 0.1736 g, 0.626 mmol, 33% yield) of the product

Sources & evidence

ORD record
ord-1e797c06be0a4e2d90436a2419be0baf
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

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