[51479-73-3] C₅H₆Cl₃NO (MW 202.47)

InChI = 1S/C5H6Cl3NO/c1-2-3-10-4(9)5(6,7)8/h2,9H,1,3H2

InChIKey = UJYZRNWTLPBNOR-UHFFFAOYSA-N

(delivers allyl group under mild conditions;² used in the preparation of N-containing intermediates¹)

Physical Data: bp 74 °C/11 mmHg.

Solubility: sol hexane, ether, dichloromethane.

Preparative Methods: typical procedure:² Sodium Hydride (0.5 g, 21 mmol) is slurried in anhydrous ether (20 mL) under a nitrogen blanket. Allyl alcohol (210 mmol) is introduced in ether (30 mL) dropwise with stirring to the slurry. After 20 min, the homogeneous solution is cooled to 0 °C and Trichloroacetonitrile (20 mL, 200 mmol) is added over 15 min. The mixture is allowed to warm to 20 °C over 60 min and then concentrated to a syrup. Pentane (20 mL) containing methanol (0.8 mL, 21 mmol) is added followed by vigorous shaking, filtration, and concentration of the filtrate and pentane washings (2 × 20 mL). The product imidate is obtained as a clear liquid (90–97%). No further purification is required. Alternatively, the imidate can be prepared by using sodium methoxide as a catalyst instead of sodium hydride. Other procedures for the preparation of allyl trichloroacetimidate have been reported.^{3, 4}

Handling, Storage, and Precautions: allyl trichloroacetimidate can be stored in solutions of hexane for up to 2 months at 0 °C. Preparation of allyl trichloroacetimidate should be performed in a well ventilated hood to avoid exposure to trichloroacetonitrile vapors.