Methanol → HCID 53840544, compound

Participants

Reaction Conditions

Reaction Steps

20 ml of borane/dimethyl sulfide complex (BMS) are added dropwise to a solution of 61.5 g of methyl 2-benzylmercapto-3-formylaminobenzoate (cf. Example d)) in 100 ml of CHCl3 at 0° C. The mixture is subsequently heated at 60° C. for 2 h, a further 20 ml of BMS are added, and the mixture is stirred at this temperature for a further 2.5 h. Then 30 ml of MeOH are added dropwise at 0° C. The mixture is transferred to a separating funnel, washed with water and brine and then dried over MgSO4. Volatile components are removed by distillation to give 54.60 g of methyl 2-benzylmercapto-3-methylaminobenzoate in the form of a yellowish oil. 1H NMR (CDCl3, 80 MHz): δ:2.6 (d, 3H, NH-CH3), 3.8 (s, 3H, OCH3), 3.9 (s, 2H, SCH2Ph), 5.2 (s, broad, 1H, NH-Me), 6.5 (d, 1H, Harom.), 6.8 (d, 1H, Harom.), 7.0-7.4 (m, 6H, Harom.).

Provenance & Evidence