Benzeneacetamide, 4-chloro-N-(1,1-dimethylethyl)- synthesis
- Product Name:Benzeneacetamide, 4-chloro-N-(1,1-dimethylethyl)-
- CAS Number:349415-65-2
- Molecular formula:C12H16ClNO
- Molecular Weight:225.71
Yield:349415-65-2 92%
Reaction Conditions:
with iron (III) perchlorate monohydrate in neat (no solvent) at 80; for 2 h;Ritter Amidation;
Steps:
Typical Experimental Procedure for the Reaction of Nitrilesand di-tert-Butyl Malonate
General procedure: A mixture of 2-(3, 4-dichlorophenyl)acetonitrile (5 mmol), ditert-butyl malonate (3 mmol), and Fe(ClO4)3·H2O (5 mol%) wasplaced in a round-bottomed flask. Then, the reaction mixturewas heated at 80 °C for 5 h. After completion of the reactionmonitored by thin layer chromatography (TLC), water (10 mL)was added and the reaction mixture was extracted with ethylacetate (3 × 20 mL). The organic layers were collected, combined,washed with water (3 × 20 ml), dried over anhydrousNa2SO4, and concentrated under vacuum. The pure product wasobtained by directly passing through a silica gel (200-300mesh) column to give a white powder 1m (1.08 g, 84% yield).Compound 1m1H NMR (400 MHz, CDCl3): δ = 7.41-7.35 (m, 2 H), 7.12-7.10 (m,1 H), 5.31 (s, 1 H), 3.40 (s, 2 H), 1.32 (s, 9 H) ppm. 13C NMR (100MHz, CDCl3): δ = 168.9, 135.6, 132.7, 131.2, 131.2, 130.6, 128.6,51.6, 43.5, 28.7 ppm. HRMS: m/z calcd for C12H15Cl2NO [M + H]+:259.0531; found: 259.0533.
References:
Feng, Chengliang;Yan, Bin;Yin, Guibo;Chen, Junqing;Ji, Min [Synlett,2018,vol. 29,# 17,p. 2257 - 2264]
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