Hydrochloric Acid → 2-(2-Iodophenyl)propanamide
Reaction equation
[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]Participants
Reactant 6
Product 1
Reagents, catalysts & solvents 2
Procedure
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]+.
Workup
- customThe volatiles were removed under reduced pressure before sat. aq. NaHCO3 (100 mL)
- additionwas added to the residue
- extractionThe aqueous phase was extracted with EtOAc (3×100 mL)
- washthe combined organics were washed with brine
- dry with materialdried over MgSO4
- customthe volatiles were removed in vacuo
Sources & evidence
- ORD record
- ord-c331bba519b8463eaa897cac4789a061
- Source dataset
- uspto-grants-2016_01
- Patent number
- US09238644B2
Reaction notes
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