Water → Cyclopropanecarboxylic acid(5-bromo-2-iodo-benzyl)-ethyl-amide

HRID 1625673Notes

Reaction equation

HRID 1625673 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([I:12])=[C:6]([CH:11]=1)[CH2:7][NH:8][CH2:9][CH3:10].C(N(CC)C(C)C)(C)C.[CH:22]1([C:25](Cl)=[O:26])[CH2:24][CH2:23]1.O>ClCCl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([I:12])=[C:6]([CH:11]=1)[CH2:7][N:8]([CH2:9][CH3:10])[C:25]([CH:22]1[CH2:24][CH2:23]1)=[O:26]

Participants

6

Reactant 4

HCID 962WaterHCID 77637Cyclopropanecarbonyl chlorideHCID 81531DiisopropylethylamineHCID 58148919(5-Bromo-2-iodo-benzyl)-ethyl-amine

Product 1

HCID 58149034Cyclopropanecarboxylic acid(5-bromo-2-iodo-benzyl)-ethyl-amide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

(5-Bromo-2-iodo-benzyl)-ethyl-amine (5.0 g, 14.7 mmol) was dissolved in dichloromethane (75 mL) along with N,N-diisopropylethylamine (5.12 mL, 29.4 mmol). The solution was cooled to 0° C. and cyclopropanecarbonyl chloride (1.41 mL, 15.4 mmol) was added. The reaction was monitored by analytical LCMS and after 15 minutes water was added and the layers were separated. The organic layer was dried with magnesium sulfate then filtered and concentrated to afford the title compound, which was used without further purification.

Workup

  1. customthe layers were separated
  2. dry with materialThe organic layer was dried with magnesium sulfate
  3. filtrationthen filtered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-25da86860178472eb61874c672942ef6
Source dataset
uspto-grants-2014_07
Patent number
US08785393B2

Reaction notes

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