1,1'-Thiocarbonyldiimidazole → Ethyl N-methyl-N-(4-isothiocyanatophenyl)glycinate

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Reaction Steps

A solution of 14.7 g (66 mmol) of ethyl N-methyl-N-(4-nitrosophenyl)glycinate in 200 mL of ethyl acetate was reduced (10% Pd/C, 50 psi H2) until uptake was complete, dried 1 hr (Na2SO4), filtered, concentrated, and dissolved in a solution of 12.5 g (70mmol) of thiocarbonyldimidazole in 100 mL CH2Cl2/300 ml toluene. When tlc showed only product (2 hr ,Rf 0.6,CH2Cl2), the solution was washed with 2×100 mL of water, passed throug a silica plug to remove color, and recrystallized from hexane (300 mL) to give 13.6 g (54 mmol, 82%) mp 90-91°. Anal. C12H14N2O2S (250): Calcd.: C,57.58; H,5.64; N,11.19; S,12.81. Found: C,57.63; H,5.59; N,11.17; S,12.49. MS(FD) m/z 250. 1H NMR(CDCl3)δ: 7.10,d,2H,ArH; 6.58,d,2H,ArH; 4.18,q,2H,CH2—O; 4.05,s,2H,CH2—N; 3.07,s,3H,CH3—N; 1.25,s,3H,CH3—C.

Provenance & Evidence