Hydrochloric Acid → 2-(2-Iodophenyl)propanamide

HRID 592353Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 592353
[I:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([CH3:12])[C:9](O)=[O:10].CC[N:15](C(C)C)C(C)C.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.Cl.C(=O)([O-])[O-].[NH4+].[NH4+]>C1COCC1.CN(C=O)C>[I:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([CH3:12])[C:9]([NH2:15])=[O:10]

Komponenten

9

Edukt 6

HCID 313Hydrochloric AcidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 517111Ammonium CarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 222368512-(2-Iodophenyl)propanoic acid

Produkt 1

HCID 867122772-(2-Iodophenyl)propanamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 2-(2-iodophenyl)propanoic acid (9.73 g, 35.2 mmol) in THF (24 mL), DMF (4 mL) and DIPEA (30.7 mL, 0.176 mol) was stirred with HOBt (7.14 g, 52.9 mmol) and EDCl.HCl (10.1 g, 52.9 mmol) for 10 minutes at room temperature under N2. Ammonium carbonate (16.9 g, 0.176 mol) was then added and the reaction mixture was stirred overnight at room temperature. The volatiles were removed under reduced pressure before sat. aq. NaHCO3 (100 mL) was added to the residue. The aqueous phase was extracted with EtOAc (3×100 mL) and the combined organics were washed with brine, dried over MgSO4 and the volatiles were removed in vacuo to give the impure title compound I13 as a pale yellow solid (˜95% purity, 10.05 g, >95%). LCMS-D: rt 3.12 min; m/z 276 [M+H]+.

Aufarbeitung

  1. customThe volatiles were removed under reduced pressure before sat. aq. NaHCO3 (100 mL)
  2. additionwas added to the residue
  3. extractionThe aqueous phase was extracted with EtOAc (3×100 mL)
  4. washthe combined organics were washed with brine
  5. dry with materialdried over MgSO4
  6. customthe volatiles were removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-c331bba519b8463eaa897cac4789a061
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09238644B2

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