2-(2-NAPHTHYLTHIO)ACETONITRILE synthesis
- Product Name:2-(2-NAPHTHYLTHIO)ACETONITRILE
- CAS Number:5324-69-6
- Molecular formula:C12H9NS
- Molecular Weight:199.27
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Yield:5324-69-6 65%
Reaction Conditions:
in acetone;
Steps:
5.1 (Step 1)
(Step 1) Preparation of 2-Naphthalenylthioacetonitrile To a stirred suspension of 2-naphthalenethiol (7.20 g, 45 mmol) and K2 CO3 (6.90 g, 50 mmol) in acetone (350 mL) was added chloroacetonitrile (3.78 g, 50 mmol) in acetone (50 mL) dropwise over 30 minutes. The resulting yellow mixture was stirred at room temperature for 18 hours. The volatiles were removed in vacuo and the residue was partitioned between EtOAc (300 mL) and H2 O (300 mL). The aqueous phase was washed with EtOAc (1*250 mL) and the combined extracts were dried (Na2 SO4) and concentrated in vacuo. The crude material was purified by preparative HPLC (SiO2: gradient EtOAc/hexane) to give the title compound as a light brown solid (5.86 g, 65%). NMR (200 MHz, CDCl3): δ 8.05 (s, 1H), 7.81 (m, 3H), 7.54 (m, 3H), 3.61 (s, 2H).
References:
US4895861,1990,A
