Hydrochloric Acid → 1-(3-Bromophenyl)cyclopropane-1-carboxamide

HRID 592456Notes

Reaction equation

HRID 592456 reaction equation
[C:1](=[O:4])([O-])[O-].[NH4+].[NH4+].[Br:7][C:8]1[CH:9]=[C:10]([C:14]2(CC(O)=O)[CH2:16][CH2:15]2)[CH:11]=[CH:12][CH:13]=1.C1C=CC2N(O)N=[N:27]C=2C=1.CCN=C=NCCCN(C)C.Cl.Cl>CCN(CC)CC.CN(C=O)C.CCOC(C)=O>[Br:7][C:8]1[CH:9]=[C:10]([C:14]2([C:1]([NH2:27])=[O:4])[CH2:16][CH2:15]2)[CH:11]=[CH:12][CH:13]=1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 757711-HydroxybenzotriazoleHCID 517111Ammonium CarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 82088576HCID 82088576, compound

Product 1

HCID 210628891-(3-Bromophenyl)cyclopropane-1-carboxamide

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

Ammonium carbonate (7.97 g 83.0 mmol) was added to a suspension of 1-(3-bromophenyl)cyclopropylacetic acid (2.00 g, 8.30 mmol), HOBt (1.68 g, 12.4 mmol) and EDCl.HCl (2.39 g, 12.4 mmol) in Et3N (5 mL) and DMF (25 mL) and the mixture was stirred at room temperature overnight. EtOAc (150 mL) was added and the organic layer was washed with sat. NaHCO3 solution (100 mL), 0.5 M citric acid solution (3×100 mL), water (100 mL), brine (50 mL) and dried (Na2SO4). The volatiles were removed in vacuo to yield the title compound A58 as a white solid (1.78 g, 89%). LCMS-A: rt 5.807 min; m/z 241 [M+H]+.

Workup

  1. washthe organic layer was washed with sat. NaHCO3 solution (100 mL), 0.5 M citric acid solution (3×100 mL), water (100 mL), brine (50 mL)
  2. dry with materialdried (Na2SO4)
  3. customThe volatiles were removed in vacuo

Sources & evidence

ORD record
ord-4a1d235037984a289de3733c85f29ab0
Source dataset
uspto-grants-2016_01
Patent number
US09238644B2

Reaction notes

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