ChemicalBook CAS DataBase List (S)-(+)-2,2-Dimethylcyclopropanecarboxamide

(S)-(+)-2,2-Dimethylcyclopropanecarboxamide synthesis

8synthesis methods

Product Name:(S)-(+)-2,2-Dimethylcyclopropanecarboxamide
CAS Number:75885-58-4
Molecular formula:C6H11NO
Molecular Weight:113.16

14590-53-5 Synthesis

(S)-(+)-2,2-DIMETHYLCYCLOPROPANE CARBOXYLIC ACID

14590-53-5
109 suppliers
$22.00/1g

(S)-(+)-2,2-Dimethylcyclopropanecarboxamide

75885-58-4
262 suppliers
$5.00/1g

Yield:75885-58-4 92.1%

Reaction Conditions:

Stage #1: (+)-1S-2,2-dimethylcyclopropane-carboxylic acidwith thionyl chloride in dichloromethane at 20;
Stage #2: with ammonia in dichloromethane at -15;

Steps:

3 Example 3

28. 5g of S-2,2-dimethylcyclopropane carboxylic acid and 114g of dichloromethane were added to a [1,] [OOOML] round bottom flask with an agitator, a condenser and a thermometer. 29.7g of thionylchloride was slowly added into the flask while maintaining the solution at room temperature. After the gas-generation reaction was completed, 12.8g of ammonia was added while keeping the temperature [AT-15°C.] After the reaction was completed, the reactants were added by 200mL of water and agitated for 15 minutes. Then, the organic phase was separated from the aqueous phase and further distilled so that the solvent and organic materials with low boiling point were recovered and S-2,2- dimethylcyclopropane carboxamide was obtained. The obtained S-2,2- dimethylcyclopropane carboxamide was recrystalized in methanol so as to obtain a white crystalline powder of purified S-2,2-dimethylcyclopropane carboxamide (yield : 92. [1%,] purity: 99.4%, optical purity: 99.5%). Rf = 0. 3 (n-hexane/ethyl acetate, 1/1) . 1 H NMR (CDC13, 300MHZ) : 5.59 (BR, S, 2H, ); 1.29 (DD, 1H, J=7.91 HZ, J=5.40 HZ); 1.17 (s, 3H); 1.12 (s, 3H); 1.06 (dd, 1H, J=5.40 Hz, J=4.84 Hz); 0.74 (dd, 1H, J=7.92 Hz, J=4.34 Hz)

References:

WO2004/5241,2004,A1 Location in patent:Page 10