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. 2012 Jan 10;8:61–70. doi: 10.3762/bjoc.8.6

Table 2.

Preparation of isothiocyanatesa.

graphic file with name Beilstein_J_Org_Chem-08-61-i001.jpg

entry substrate product timeb (h) yieldc (%)

1 graphic file with name Beilstein_J_Org_Chem-08-61-i002.jpg graphic file with name Beilstein_J_Org_Chem-08-61-i003.jpg 1 85
2 graphic file with name Beilstein_J_Org_Chem-08-61-i004.jpg graphic file with name Beilstein_J_Org_Chem-08-61-i005.jpg 1 94
3 graphic file with name Beilstein_J_Org_Chem-08-61-i006.jpg graphic file with name Beilstein_J_Org_Chem-08-61-i007.jpg 1 80
4 graphic file with name Beilstein_J_Org_Chem-08-61-i008.jpg graphic file with name Beilstein_J_Org_Chem-08-61-i009.jpg 1 95
5 graphic file with name Beilstein_J_Org_Chem-08-61-i010.jpg graphic file with name Beilstein_J_Org_Chem-08-61-i011.jpg 1 98
6 graphic file with name Beilstein_J_Org_Chem-08-61-i012.jpg graphic file with name Beilstein_J_Org_Chem-08-61-i013.jpg 1 95
7 graphic file with name Beilstein_J_Org_Chem-08-61-i014.jpg graphic file with name Beilstein_J_Org_Chem-08-61-i015.jpg 1 99
8 graphic file with name Beilstein_J_Org_Chem-08-61-i016.jpg graphic file with name Beilstein_J_Org_Chem-08-61-i017.jpg 1 99
9 graphic file with name Beilstein_J_Org_Chem-08-61-i018.jpg graphic file with name Beilstein_J_Org_Chem-08-61-i019.jpg 3 98 (94)
10 graphic file with name Beilstein_J_Org_Chem-08-61-i020.jpg graphic file with name Beilstein_J_Org_Chem-08-61-i021.jpg 3 86
11 graphic file with name Beilstein_J_Org_Chem-08-61-i022.jpg graphic file with name Beilstein_J_Org_Chem-08-61-i023.jpg 3 93
12 graphic file with name Beilstein_J_Org_Chem-08-61-i024.jpg graphic file with name Beilstein_J_Org_Chem-08-61-i025.jpg 3 95
13 graphic file with name Beilstein_J_Org_Chem-08-61-i026.jpg graphic file with name Beilstein_J_Org_Chem-08-61-i027.jpg 3 98
14 graphic file with name Beilstein_J_Org_Chem-08-61-i028.jpg graphic file with name Beilstein_J_Org_Chem-08-61-i029.jpg 12 81d
15 graphic file with name Beilstein_J_Org_Chem-08-61-i030.jpg graphic file with name Beilstein_J_Org_Chem-08-61-i031.jpg 20 70d

aReaction conditions: 20 mmol of amine substrate, 24 mmol of CS2, 40 mmol of K2CO3, room temperature. HPLC monitored the conversion. After the amine was totally consumed, the mixture was cooled to 0 °C, and 10 mmol of TCT in CH2Cl2 was added dropwise. The mixture was stirred for another 0.5 h and basified to pH >11 with 6 N NaOH. bThe reaction time for the first step. cIsolated yield. Data in the parenthesis is the isolated yield in 1-mol scale. d3.0 equiv of CS2 was used and the reaction temperature was 40 °C.