Amination of Aryl Halides and Esters Using Intensified Continuous Flow Processing.

Amination of Aryl Halides and Esters Using Intensified Continuous Flow Processing.

Molecules (Basel, Switzerland) (2015-10-02)

Thomas M Kohl, Christian H Hornung, John Tsanaktsidis

ABSTRACT

Significant process intensification of the amination reactions of aryl halides and esters has been demonstrated using continuous flow processing. Using this technology traditionally difficult amination reactions have been performed safely at elevated temperatures. These reactions were successfully conducted on laboratory scale coil reactor modules with 1 mm internal diameter (ID) and on a preparatory scale tubular reactor with 6 mm ID containing static mixers.

MATERIALS

Product Number

Brand

Product Description

V900090

Sigma-Aldrich

Dimethyl sulfoxide, Vetec^™, reagent grade, 99%

676853

Sigma-Aldrich

Dichloromethane, ACS reagent, ≥99.5%, contains 40-150 ppm amylene as stabilizer

673773

Sigma-Aldrich

2-Propanol, ACS reagent, ≥99.5%

109827

Sigma-Aldrich

2-Propanol, Laboratory Reagent, ≥99.5%

I9030

Sigma-Aldrich

Isopropyl alcohol, meets USP testing specifications

D65100

Sigma-Aldrich

Dichloromethane, contains 40-150 ppm amylene as stabilizer, ACS reagent, ≥99.5%

D5879

Sigma-Aldrich

Dimethyl sulfoxide, ReagentPlus^®, ≥99.5%

190764

Sigma-Aldrich

2-Propanol, ACS reagent, ≥99.5%

24137

Sigma-Aldrich

2-Propanol, puriss., meets analytical specification of Ph. Eur., BP, USP, ≥99.5% (GC)

24233

Sigma-Aldrich

Dichloromethane, puriss., meets analytical specification of Ph. Eur., NF, ≥99% (GC)

472301

Sigma-Aldrich

Dimethyl sulfoxide, ACS reagent, ≥99.9%

41640

Sigma-Aldrich

Dimethyl sulfoxide, puriss. p.a., ACS reagent, ≥99.9% (GC)

59300

Sigma-Aldrich

2-Propanol, puriss. p.a., ACS reagent, ≥99.8% (GC)

494453

Sigma-Aldrich

Dichloromethane, biotech. grade, 99.9%, contains 40-150 ppm amylene as stabilizer

33539

Sigma-Aldrich

2-Propanol, puriss. p.a., ACS reagent, reag. ISO, reag. Ph. Eur., ≥99.8% (GC)

34943

Sigma-Aldrich

Dimethyl sulfoxide, puriss. p.a., dried, ≤0.02% water

320269

Sigma-Aldrich

Dichloromethane, ACS reagent, ≥99.5%, contains 40-150 ppm amylene as stabilizer

32222

Sigma-Aldrich

Dichloromethane, puriss. p.a., ACS reagent, reag. ISO, ≥99.9% (GC)

15-2360

Sigma-Aldrich

2-Propanol, suitable for HPLC

673439

Sigma-Aldrich

Dimethyl sulfoxide solution, 50 wt. % in H₂O

15-2320

Sigma-Aldrich

2-Propanol, JIS special grade, ≥99.5%

07-4872

Sigma-Aldrich

Dimethyl sulfoxide, ≥99.0%, suitable for absorption spectrum analysis

07-4860

Sigma-Aldrich

Dimethyl sulfoxide, JIS special grade, ≥99.0%

07-4870

Sigma-Aldrich

Dimethyl sulfoxide, SAJ first grade, ≥99.0%

07-4875

Sigma-Aldrich

Dimethyl sulfoxide, ≥99.5%

07-2180

Sigma-Aldrich

Dichloromethane, JIS special grade, ≥99.0%

15-2330

Sigma-Aldrich

2-Propanol, SAJ first grade, ≥99.0%

07-2190

Sigma-Aldrich

Dichloromethane, SAJ first grade, ≥99.0%

07-4871

Sigma-Aldrich

Dimethyl sulfoxide, suitable for HPLC

723851

Supelco

Dichloromethane solution, contains 10 % (v/v) methanol