Hydrochloric Acid → 1-(2-Iodophenyl)cyclopropanecarboxamide

HRID 592350Notes

Reaction equation

HRID 592350 reaction equation
C1C=CC2N(O)N=[N:7]C=2C=1.CCN=C=NCCCN(C)C.Cl.Cl.[I:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[C:31]1([C:34]([OH:36])=O)[CH2:33][CH2:32]1.CCN(CC)CC.C(=O)([O-])[O-].[NH4+].[NH4+]>CN(C=O)C.C1COCC1>[I:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[C:31]1([C:34]([NH2:7])=[O:36])[CH2:33][CH2:32]1

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 517111Ammonium CarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 200261901-(2-Iodophenyl)cyclopropane-1-carboxylic acid

Product 1

HCID 867122741-(2-Iodophenyl)cyclopropanecarboxamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

HOBt (1.89 g, 14.0 mmol) and EDCl.HCl (2.69 g, 14.0 mmol) were added to a solution of 1-(2-iodophenyl)cyclopropanecarboxylic acid (I10) (3.11 g, 10.8 mmol) in DMF (6 mL), THF (29 mL) and Et3N (9.4 mL, 54 mmol). After 15 minutes ammonium carbonate (7.95 g, 86.4 mmol) was added and the resulting mixture was stirred at room temperature for 20 hours. The volatiles were removed in vacuo and water (150 mL) was added to the residue resulting in the formation of a suspension. The suspension was sonicated for several minutes, filtered and the filter cake dried to give the title compound I11 as an off white solid (2.55 g, 82%); 1H NMR (300 MHz, d6-DMSO) δ 7.87 (d, J=7.6 Hz, 1H), 7.36-7.38 (m, 2H), 7.02-7.08 (m, 1H), 6.96 (brs, 1H), 6.05 (brs, 1H), 1.52 (brs, 2H), 0.96 (brs, 2H). LCMS-B: rt 5.800 min; m/z 288 [M+H]+.

Workup

  1. customThe volatiles were removed in vacuo and water (150 mL)
  2. additionwas added to the residue
  3. customresulting in the formation of a suspension
  4. customThe suspension was sonicated for several minutes
  5. filtrationfiltered
  6. customthe filter cake dried

Sources & evidence

ORD record
ord-91cd16fb2a3a49d3b6c03516463ad12b
Source dataset
uspto-grants-2016_01
Patent number
US09238644B2

Reaction notes

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