US EPA

7458355 

Journal Article 

New method for the synthesis of sulforaphane and related isothiocyanates 

Chen, X; Li, Z; Sun, X; Ma, H; Chen, X; Ren, J; Hu, K 

2011 

1 

Synthesis
ISSN: 0039-7881
EISSN: 1437-210X 

24 

3991-3996 

English 

10.1055/s-0031-1289601 

The biologically important isothiocyanate sulforaphane (4- isothiocyanatobutyl methyl sulfoxide) was synthesized in six simple steps from commercially available 4-aminobutan-1-ol with an overall yield of 64%. The new synthetic method is suitable for multigram-scale preparation of sulforaphane and does not require expensive or toxic reagents. A novel one-pot procedure was also developed for preparing isothiocyanates through reaction of amines with O-phenyl chlorothioformate under mild conditions. Additionally, methyl pyrrolidine-1-carbodithioate was obtained as an unexpected byproduct, and this protocol was shown to be useful for the synthesis of S-aryl or S-heterocyclic thiocarbamates with cyclic side chains. © Georg Thieme Verlag Stuttgart · New York. 

antitumor agents; isothiocyanates; sulforaphane; thiocarbamates; Anti-tumor agents; Isothiocyanates; One-pot procedures; Side-chains; Sulforaphane; Synthetic methods; Thiocarbamates; Toxic reagents; Chemistry; Speech synthesis; Synthesis (chemical); (isothiocyanatomethyl)benzene; 1 isothiocyanato 4 (methylsulfanyl)butane; 1 isothiocyanato 4 methoxybenzene; 1 isothiocyanato 4 methylbenzene; 1 isothiocyanatobutyl mesylate; 1 isothiocyanatohexane; 4 (methylsulfanyl)butan 1 amine; 4 aminobutan 1 ol; 4 hydroxybutyl isothiocyanate; alcohol derivative; amine; formic acid derivative; heterocyclic compound; isocyanic acid derivative; isothiocyanatobenzene; isothiocyanatocyclohexane; methyl pyrrolidine 1 carbodithioate; o phenyl chlorothioformate; reagent; sulforaphane; tert butyl (4 hydroxybutyl)carbamate; tert butyl [4 (methylsulfanyl)butyl]carbamate; thiocarbamic acid derivative; unclassified drug; article; chemical reaction; drug design; one pot synthesis; reaction analysis; synthesis