Triethylamine → HCID 54384183, compound

Participants

Reaction Steps

To a solution of 22.8 g of N'-(4-cyano-3-isopropyl- 5-isothiazolyl)-N,N-dimethylurea in 300 ml of benzene was added 83.3 g of phosphorous oxybromide. The solution was cooled to 0° and 14 ml (9.7 g) of triethylamine was added. The ice-bath was removed and the reaction mixture was heated under reflux overnight. The following day the reaction mixture was filtered through sintered glass. The filtrate was washed with two 200 ml portions of cold water and two 200 ml portions of saturated sodium bicarbonate solution. Two hundred milliliters of chloroform was added to aid in separation of the organic phase from the final wash. The separated organic phase was dried, then concentrated under reduced pressure. The residue was passed over a column of 300 grams of silica gel with chloroform as the eluant. The first ten 250 ml fractions were evaporated to produce a yellow solid, mp 93°-97°. The combined residues were recrystallized from 175 ml of cyclohexane to yield 13.8 g of N'-(4 -cyano-3-isopropyl-5-isothiazolyl)-N,N-dimethylbromoformamidine mp 92°-96°. The ir and nmr spectra were consistent with the assigned structure.

Provenance & Evidence