Chloroacetone → HCID 20321411, compound

Participants

Reaction Steps

A mixture of p-methoxybenzyl N-thioformyl-glycinate (4.79 g., 20 mMols), anhydrous powdered K2CO3 (8.29 g., 60 mMols), Me2CO (50 ml.), and ClCH2COCH3 (2.0 ml., 25 mMols) is stirred in a capped flask at room temperature for 6.5 hrs. The mixture is diluted with EtOAc (100 ml.) and filtered. The filtrate is evaporated in vacuo to an oil which is taken up in Et2O, washed twice with H2O and brine, dried with MgSO4, filtered, and evaporated in vacuo to an orange semi-solid (5.36 g.). The crude product is dissolved in warm PhH (25 ml.) and the solution is left in a refrigerator. The pale yellow crystals of p-methoxybenzyl 5-hydroxy-5-methyl-5,6-dihydro-4H-1,3-thiazine-4-carboxylate (2.23 g.) are collected, washed with cold PhH and petroleum ether, and dried in vacuo: mp 102°-103° C. (micro hot stage); ir (CHCl3) 2.97, 5.82, 6.21, 6.62, 7.97, 8.51, 9.62, and 12.04μ; nmr (CDCl3) δ1.35 (s, 3, CH3), 2.75 (d of d, l, J=12 Hz and J=1Hz, SCH), 3.07 (d, l, J=12Hz, SCH), 3,25 (br s, l, OH), 3.82 (s, 3, OCH3), 4.17 (d of d, l, J=2Hz and J=1Hz, H4), 5.18 (s, 2, CH2Ar), 6.87 and 7.33 (two d's 4, J=9Hz, ArH), and 8.23 (d, l, J=2Hz, H2); mass spectrum m/e 295 (M+), 222, 131, and 121.

Provenance & Evidence