1-Methyl-1-acetyl-4-{4-(N-methyl-N-carboethoxymethylamino)phenyl}-3-thiosemicarbazide → HCID 178472693, compound

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Reaction Steps

A solution of 2.03 g (6.06 mmol) of 1-methyl-1-acetyl-4-{4-(N-methyl-N-carboethoxymethylamino)phenyl}-3-thiosemicarbazide in 50 ml of butanol was heated at reflux until tlc showed no starting material (Rf 0.3,EtOAc,5 hr). Solvent was distilled and the residue crystallized with ethyl acetate. The solid (1.2 g) was recrystallized from 25 ml of water to give 0.978 g (3.05 mmol,50%), mp 211°. Anal. C15H20N4O2S (320): Calcd.: C,56.23; H,6.29; N,17.49; S,10.01. Found: C,56.30; H,6.20; N,17.93; S,9.61. MS(FD) 320. 1H NMR (DMSO-d6):δ 7.08,d,2H,ArH; 6.71,d,2H,ArH; 4.23,s,2H, CH3--N; 4.08,q,2h,CH2--O; 3.68,s,3H,CH3--N+ ; 3.29,s,3H,CH3--N; 2.23,s,3H,CH3--C=; 1.16,t,3H,CH3--C.

Provenance & Evidence