Tetrahydrofuran → HCID 57855982, compound

Participants

Reaction Steps

3-chloro-5-nitro-2,4-bis-(2-trimethylsilanyl-ethylsulfanyl)-benzoic acid methyl ester) in a ratio 74:36 (NMR integrals), are suspended in 16 ml of EtOH and 20 ml of MeOH. Then, 16 ml of a saturated NH4Cl aqueous solution are added followed by 20 ml of THF. 788 mg (0.012 mol, 4.4 eq.) of dust powdered zinc are added and the reaction is stirred during 1 h 30. 50 ml of a saturated NH4Cl aqueous solution are added to the mixture and the product is extracted with CH2Cl2 (3 times). The regrouped organic phases are dried with Na2SO4, filtered and evaporated. A column chromatography purification on silica gel with hexanes and EtOAc gave 680 mg (78%) of pure 2,5-diamino-3-chloro-4-(2-trimethylsilanyl-ethylsulfanyl)-benzoic acid methyl ester; 1H-NMR (CDCl3, 300 MHz): 0.02 (s, 9H), 0.78-0.89 (m, 2H), 2.83-2.91 (m, 2H), 3.88 (s, 3H), 7.33 (d, 1H) ppm.

Provenance & Evidence