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ChemicalBook CAS DataBase List 2-(Methanesulfonylamino)benzonitrile
50790-29-9

2-(Methanesulfonylamino)benzonitrile synthesis

6synthesis methods
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Yield:50790-29-9 92%

Reaction Conditions:

Stage #1: 2-benzonitrilewith sodium hydroxide;N-benzyl-N,N,N-triethylammonium chloride in tetrahydrofuran;water at 25; for 20 h;
Stage #2: with hydrogenchloride in tetrahydrofuran;water;

Steps:

1 Preparation of N-(2-Aminomethyl-phenyl)-methanesulfonamide acetate (B7)

Step 1. Preparation of N-(2-cyano-phenyl)-methanesulfonamide (B7-1): A solution of B6-1 (4 g, 14.8 mmol) in THF (29.26 mL) was treated with 40% aqueous NaOH (29.26 mL) and BTEAC (0.331 g, 1.45 mmol) and stirred at 25° C. for 20 hours. The reaction mixture was then concentrated, and the resultant residue was diluted with water (100 mL) and neutralized with 6N HCl (30 mL). The mixture was extracted with DCM (200 mL), and the organic layer was washed with water (150 mL) and brine. The organic solution was then dried over anhydrous sodium sulfate and concentrated to provide B7-1 as a white solid. Yield: 2.8 g, 92%. 1H NMR (CDCl3): δ 7.7-7.76 (m, 1H), 7.6-7.65 (m, 1H), 6.8-6.98 (broad, 1H) and 3.14 (s, 3H). Mass: (M-1) 195 calculated for C8H8N2O2S.

References:

US2009/54395,2009,A1 Location in patent:Page/Page column 38