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N,N-dimethyl-aniline; trichlorophosphate Chlorination; 2 h; Heating;

1: trichlorophosphate / N,N-dimethyl-aniline 2: m-chloro-peroxy-benzoic acid / water; 4-(dicyanomethylene)-2-methyl-6-(4-dimethylaminostyryl)-4H-pyran; methanol View Scheme

1: 87 percent / POCl3; N,N-dimethylaniline / 2 h / Heating 2: 98 percent / Zn; NH4Cl; H2O / benzene / 8 h / Heating 3: 87 percent / MCPBA / CH2Cl2 / 20 °C 4: 74 percent / NaOH; H2O / 50 °C View Scheme

1: 87 percent / POCl3; N,N-dimethylaniline / 2 h / Heating 2: 98 percent / Zn; NH4Cl; H2O / benzene / 8 h / Heating 3: 87 percent / MCPBA / CH2Cl2 / 20 °C View Scheme