Ethyl Acetate → HCID 67429319, compound

HRID 1661086Notes

Reaction equation

HRID 1661086 reaction equation
[NH2:1][C:2]1[C:11]([I:12])=[CH:10][C:9]([Cl:13])=[CH:8][C:3]=1[C:4]([O:6]C)=O.[NH2:14][CH:15]([CH2:19][CH2:20][CH3:21])[CH2:16][CH2:17][CH3:18].C[Al](C)C.C(OCC)(=O)C>C1(C)C=CC=CC=1>[NH2:1][C:2]1[C:11]([I:12])=[CH:10][C:9]([Cl:13])=[CH:8][C:3]=1[C:4]([NH:14][CH:15]([CH2:19][CH2:20][CH3:21])[CH2:16][CH2:17][CH3:18])=[O:6]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 386654-HeptanamineHCID 7020924Methyl 2-amino-5-chloro-3-iodobenzoateHCID 16682925Trimethylaluminum

Product 1

HCID 67429319HCID 67429319, compoundYield 315.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
100 °C

Procedure

Added successively to a solution of 3 g of methyl 2-amino-5-chloro-3-iodobenzoate in 100 cm3 of toluene, under an inert atmosphere and at a temperature close to 20° C., are 2.2 g of 4-aminoheptane then 12 cm3 of a 2M solution of trimethylaluminum in toluene. The reaction mixture is heated, while stirring, for 16 h at 100° C., then it is cooled to 20° C. in order to then be poured over a mixture of 250 g of water/ice and 150 cm3 of ethyl acetate. The suspension obtained is filtered over a Celite 545 pellet. The aqueous phase is extracted with 3 lots of 100 cm3 of ethyl acetate. The organic phases are combined then washed with 100 cm3 of a saturated aqueous solution of sodium chloride, dried over magnesium sulfate and concentrated using a rotary evaporator under reduced pressure (5 kPa). The 12 g of crude product obtained are purified by flash chromatography over silica (column: 200 g; particle size: 15-40 μm; eluent: 100% dichloromethane). After concentrating the fractions under reduced pressure, 3.21 g of 2-amino-5-chloro-3-iodo-N-(1-propylbutyl)benzamide are obtained.

Workup

  1. customclose to 20° C.
  2. temperatureThe reaction mixture is heated
  3. temperatureit is cooled to 20° C. in order
  4. customThe suspension obtained
  5. filtrationis filtered over a Celite 545 pellet
  6. extractionThe aqueous phase is extracted with 3 lots of 100 cm3 of ethyl acetate
  7. washThe organic phases are combined then washed with 100 cm3 of a saturated aqueous solution of sodium chloride
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated
  10. customa rotary evaporator under reduced pressure (5 kPa)

Sources & evidence

ORD record
ord-286cce72862a425795c087c17a591759
Source dataset
uspto-grants-2011_10
Patent number
US08030320B2

Reaction notes

Loading…