Triethylamine → 1-(benzo[d][1,3]dioxol-5-yl)-N-(3-bromo-4-methoxyphenyl)cyclopropanecarboxamide

HRID 39151

Reaction equation

HRID 39151 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3([C:13](Cl)=[O:14])[CH2:12][CH2:11]3)=[CH:9][C:4]=2[O:3][CH2:2]1.[Br:16][C:17]1[CH:18]=[C:19]([NH2:25])[CH:20]=[CH:21][C:22]=1[O:23][CH3:24].CCN(CC)CC>C(Cl)Cl>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3([C:13]([NH:25][C:19]4[CH:20]=[CH:21][C:22]([O:23][CH3:24])=[C:17]([Br:16])[CH:18]=4)=[O:14])[CH2:12][CH2:11]3)=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 9610833-Bromo-4-methoxyanilineHCID 591291541-(Benzo[d][1,3]dioxol-5-yl)cyclopropanecarbonyl chloride

Product 1

HCID 592063761-(benzo[d][1,3]dioxol-5-yl)-N-(3-bromo-4-methoxyphenyl)cyclopropanecarboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a solution of the crude 1-benzo[1,3]dioxol-5-yl-cyclopropanecarbonyl chloride (3.0 mmol) in CH2Cl2 (30 mL) at ambient temperature was added a solution of 3-bromo-4-methoxybenzenamine (3.3 mmol), Et3N (15 mmol), and CH2Cl2 (90 mL) dropwise. The mixture was allowed to stir for 16 h before it was diluted with CH2Cl2 (500 mL). The solution was washed with 1N HCl (2×250 mL), sat. aq. NaHCO3 (2×250 mL), then brine (250 mL). The organics were dried over Na2SO4, filtered, and concentrated in vacuo to provide 1-(benzo[d][1,3]dioxol-5-yl)-N-(3-bromo-4-methoxyphenyl)cyclopropane-carboxamide (B-10) with suitable purity to be used without further purification.

Workup

  1. washThe solution was washed with 1N HCl (2×250 mL), sat. aq. NaHCO3 (2×250 mL)
  2. dry with materialThe organics were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5ce2af9d25eb4428b72f64e441fd3acd
Source dataset
uspto-grants-2013_09
Patent number
US08524767B2

Linked notes

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