反应详情

温度

0 °C

A solution of 9.77 g (43.65 mmol) of (E)-3,4-dichlorocinnamic acid in 250 ml of CH2Cl2 was treated at RT with 3 drops of DMF. 4.15 ml (48.02 mmol, 1.1 eq) of oxalyl chloride in 30 ml CH2Cl2 were added dropwise and stirring was continued for 3 h. The solution was evaporated, redissolved in 170 ml of CH2Cl2, cooled (0° C.) and treated with a solution of 4.48 g (39.29 mmol, 0.9 eq) of 2,3,6,7-tetrahydro-(1H)-1,4-diazepin-5(4H)-one and 12.17 ml (87.30 mmol, 2 eq) of triethylamine in 80 ml of CH2Cl2. The reaction was warmed up over night to RT, then partitioned between CH2Cl2/MeOH 9:1 (×3)/ aqueous 10% KHSO4, the organic phases were washed with aqueous saturated NaHCO3 and aqueous 10% NaCl, dried over Na2SO4 and evaporated. The residue was dissolved and evaporated with toluene and crystallized with CH2Cl2/Et2O to give 7.99 g (58%) of the title compound as white solid. MS: 312.8 (MH+, 2Cl).

1. customThe solution was evaporated
2. dissolutionredissolved in 170 ml of CH2Cl2
3. temperatureThe reaction was warmed up over night to RT
4. custompartitioned between CH2Cl2/MeOH 9:1 (×3)/ aqueous 10% KHSO4
5. washthe organic phases were washed with aqueous saturated NaHCO3 and aqueous 10% NaCl
6. dry with materialdried over Na2SO4
7. customevaporated
8. dissolutionThe residue was dissolved
9. customevaporated with toluene
10. customcrystallized with CH2Cl2/Et2O