Dimethylformamide → HCID 11688411, compound

Participants

Reaction Conditions

Reaction Steps

In a 20 L 4 necked RB Flask, fitted with a mechanical stirrer, reflux condenser, add 4-cyclopentyloxy-3(4′-nitro-2′-bromophenoxy)benzaldehyde (1.3 kg, 3.20 M), dimethyl formamide (7.8 L), sodium carbonate (0.51 kg, 4.8M) at temperature in the range of 25-35° C. under stirring. Heat the reaction mixture to temperature of 130-140° C. and add palladium acetate. Trimer (75 g, 0.11M) and maintain at temperature of 130-140° C. for 1 h under stirring. After 1 hr maintenance, the second lot of palladium acetate trimer (75 g, 0.11M) was added at temperature of 130-140° C. under stirring and maintained for 1 hr. After 2 hr maintenance the third lot of palladium acetate trimer (75 g, 0.11M) was added at temperature of 130-140° C. under stirring and maintained for 1 hr. The progress of the reaction mixture was monitored by HPLC. The reaction mixture was cooled to 70° C. and 4.7 L of THF was added to the reaction mixture and stirred for 30 min. The inorganic insolubles were filtered and washed with THF (1 L×2). Collect the THF MLS and add to DM water (15 L) under stirring. The precipitated product was filtered, washed with water (5 L) and dried in the vacuum oven at temp. below 60° C. The dried product was subjected to reflux in a mixture of THF (1.3 L) and Ethyl acetate (2.6 L) for 2 h and brought to room temperature. The precipitated product was filtered, dried in oven at temp. below 60° C. under vaccum till MC reaches <1%. The dried product appears as pale yello solid, weighs about 650-700 g , yield 60-65%, purity 97-98% by HPLC, m.p. 230-232° C. The IR (KBr) spectrum shows 3120 (CH str), 2960 (CH str), 1682 (CHO str), 1340 (NO2 str)

Provenance & Evidence