6-(THIOPHEN-2-YL)-1,3,5-TRIAZINE-2,4-DIAMINE synthesis
- Product Name:6-(THIOPHEN-2-YL)-1,3,5-TRIAZINE-2,4-DIAMINE
- CAS Number:35841-87-3
- Molecular formula:C7H7N5S
- Molecular Weight:193.23
Yield:35841-87-3 89%
Reaction Conditions:
with potassium hydroxide in dimethyl sulfoxide at 80; for 16 h;
Steps:
1 6-(thiophen-2-yl)-1,3,5-triazine-2,4-diamine
6-(thiophen-2-yl)-1,3,5-triazine-2,4-diamine (1): 2-thiophenecarbonitrile (1.90 g, 17.4 mmol), N-cyanoguanidine (1.83 g, 21.72 mmol) and KOH (0.10 g, 1.7 mmol) were put in 10 mL of DMSO. The colourless solution was heated at 80°C for 16 h and became yellow. The solvent was removed in vacuum and the crude product was triturated with cooled CH2Cl2 (4 x 100 mL at 0 °C) and extract with hot dioxane (100 mL at 100 °C). The solvent was removed in vacuum and 1 was isolated as a white solid. Yield: 2.99 g (89 %). 1H NMR (DMSO-d6): δ = 7.80 (dd, 3JH-H = 3.7, 3JH-H = 1.0, 1H, Ar), 6.93 (dd, 3JH-H = 4.8, 3JH-H = 1.0, 1H, Ar), 6.84 (dd, 3JH-H = 4.8, 3JH-H = 3.7, 1H, Ar), 6.76 (br. s, 4H, NH2 amine). 13C{1H} NMR (DMSO-d6): δ = 167.1, 166.6 (C3H4N5), 143.0, 130.4, 128.8, 128.0 (C4H3S).
References:
EP2072511,2009,A1 Location in patent:Page/Page column 6
98-03-3
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