NOTES ON SCIENTIFIC RESEARCH. 109 
ethyl (methylsulphopropyl)-thiocarbamate, the silver salt of which melts at 150° and 
which on being boiled with ethyl iodide passes into diethyl (methylsulphopropylimino)- 
thiolcarbonate. 
Through the action of acetobromoglucose on the thiourethane silver salts in 
chloroform, it was possible to synthesize the tetraacetyl compounds of the three 
glucosides from allylthiourethane (1), the thiourethane of cheiroline (II) and from benzyl- 
thiourethane (Ill). Unfortunately it was impossible to obtain the glucosides free from 
acetyl in an absolutely pure state. 
(1) ee, N: C(OC2Hs):S- Cs Hz Os (C2Hs O)s 
Tetraacetylallylthiourethane glucoside. 
(I) CHs SO; : (CHe)s : N 5 C (OC, H:) : S ° C, H, O; (Co Hs; O)4 
Tetraacetyl glucoside from cheirolinethiourethane. 
(il) C,;Hs-CHe-N:C(OC;Hs):S-CgH7Os(C2Hs O)s - 
Tetraacetylbenzylthiourethane glucoside. 
The free thiourethane glucosides are very sensitive towards saponifying agents. 
The authors further succeeded in proving that phenol cannot only be added to 
pheny! mustard oil, but likewise to allyl mustard oil, when thiourethanes are formed 
according to the scheme: R-N:CS+C,H;-OH = R:NH-CS(OC,Hs). The addition 
takes place slowly already at room temperature, more quickly on heating the 
equimolecular mixture to about 80°. When being treated with ammoniacal silver 
solution, the phenylthiourethanes afford silver salts of their pseudo-modifications: 
R-NH-CS(OC,Hs) —~ R-N:C(SAg) (OC.Hs), a quality which may be employed with 
success for the.isolation and purification of thiourethanes, as they can be obtained 
by decomposing the silver salts with hydrogen sulphide. Phenyl phenylthiocarbaminate, 
C;Hs-NH-CS(OC,Hs), melts at 142° and decomposes in contact with water little by 
little into phenol and phenyl mustard oil. It is prepared by conducting hydrogen 
sulphide into the silver salt of phenyl phenylthiocarbaminate, dissolved in chloroform. 
Said silver salt is obtained by heating equimolecular quantities of phenol and phenyl. 
mustard oil up to 80° and afterwards adding silver nitrate solution to the well-cooled 
solution; it melts at 186°. The silver salt of phenylallylthiocarbaminate, obtained in 
the same way, melts above 140°; the phenylallylthiocarbaminate, at 51°. 
It finally remains to discuss the synthesis of phenylthiourethane-d-glucoside, which 
shows great relationship with the natural mustard oil glucosides. The silver salt of 
phenylthiourethane reacts with acetobromoglucose, forming a tetraacetylthiourethane 
glucoside according to the equation: — 
SA -S- Cs Hz O5(C2 Hs O 
eeN-c") S 1} Br-CoH;Os(CsHsO). = CoHs-N: CO can Oe AaB 
‘OC2H OCH 
Phenylthiourethane ieee Acetobromoglucose. Tee comithion cae glucoside. 
On saponifying the acetyl groups with alcoholic ammonia, phenylthiourethane- 
d-glucoside is obtained in addition to acetamide. As regards hydrolysis, this glucoside 
stands half way between the thiourethane glucosides synthesized hitherto and the 
natural mustard oil glucosides (sinigrine, glucocheiroline). Whereas the thiourethane 
glucosides, which are aliphatically substituted at the nitrogen molecule, decompose 
under the formation of urethanes and thioglucose, and the mustard oil glucosides are 
split up into glucose, mustard oil, and potassium pyrosulphate, the hydrolysis of 
phenylthiourethane-d-glucoside goes on in two directions, i.e. under the formation of 
