Isothiocyanatotrimethylsilane → Isotiquimide

Participants

Reaction Steps

1.55M n-Butyl lithium in hexane (35.5 ml. 55mM) at 0° C. under argon was heated with a solution of N-benzylidine-tert-butylamine (8.85 g, 50mM) in toluene (40 ml) to form lithium N-t-butyl-N-(1-phenylpentyl) amide. After 2 hours a solution of 4-methyl-5,6,7,8-tetrahydroquinoline (7.35 g, 50mM) in toluene (10 ml) was added and after a further 0.5 hours the mixture was heated with a solution of trimethylsilyl isothio-cyanate (7.7 g, 55mM) in toluene (10 ml). After 0.5 hours the reaction was quenched with water, acidified (pH1) with sulphuric acid and the layers separated. The aqueous phase was mixed with an equal volume of cyclohexane and the pH adjusted to 10 with sodium hydroxide solution. The resultant precipitate was removed by filtration, washed with water and cyclohexane and dried in vacuo to give the title compound (7.3 g, 71%) identical with authentic material. (See Example 11 UK Patent Specification No. 1463666).

Provenance & Evidence