Essay Example on Experimental Section Efficient synthesis of some Novel

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Experimental Section Efficient synthesis of some novel 1 2 3 4 tetrahydropyrimidine 5 carboxamide derivatives in solvent free conditions under microwave irradiation N 2 Chloro 4 trifluoromethyl phenyl 4 2 methoxyphenyl 6 methyl 2 oxo 1 2 3 4 tetrahydropyrimidin 5 carboxamide 53a Conventional method To a solution of N 2 chloro 4 trifluoromethyl phenyl 3 oxobutanamide 50 0 01 mol in ethanol 30ml was sequentially added Benzaldehyde 51a 0 01 mol urea 52 0 015 mol followed by catalytic amount of p Toluenesulfonic acid and refluxed at 70 75 C for 8 5 hr After completion of the reaction monitored by TLC the reaction mixture was treated with ice cold water The resulting solid product was filtered washed with water and purified by recrystallization from ethanol to afford 53a Microwave method To a mixture of N 2 chloro 4 trifluoromethyl phenyl 3 oxobutanamide 50 0 01 mol Benzaldehyde 51a 0 01 mol urea 52 0 015 mol and a catalytic amount of p Toluenesulfonic acid was added DMF 10drops Reaction mixture was subjected to microwave irradiation for 7 0 min at 400 W On completion of reaction monitored by TLC the contents were poured into crushed ice The solid thus obtained was separated by filtration and purified by recrystallization from ethanol to produce 53a IR KBr cm 1 3410 3240 For NH 3071 For C H of Phenyl ring 2936 



C H stretching of CH3 1660 C O amide carbonyl stretching 1603 C N pyrimidine ring 1526 1469 C C Phenyl ring stretching 1344 For C N C of pyrimidine 1279 C O C asymmetrical stretching of OCH3 1030 C F stretching 1H NMR 400MHz DMSO d6 δ 2 28 s 3 H Hi 3 72 s 3 H Hii 5 15 s 1 H Hiii 6 87 s 1 H Hiv 6 97 7 14 m 2 H Hv 7 28 7 30 d 2 H Hvi 7 48 7 50 d 2 H Hviii 8 37 s 1 H Hviii 8 44 8 47 m 1 H Hix 8 90 s 1H Hl MS GC m z 440 M Anal Cacd C 54 62 H 3 90 Cl 8 06 F 12 96 N 9 55 O 10 91 Obtained Carbon 54 42 H 3 81 Cl 8 00 F 12 90 N 9 55 O 10 91 N 2 Chloro 4 trifluoromethyl phenyl 4 2 fluorophenyl 6 methyl 2 oxo 1 2 3 4 tetrahydropyrimidin 5 carboxamide 53b Conventional method To a solution of N 2 chloro 4 trifluoromethyl phenyl 3 oxobutanamide 50 0 01 mol in ethanol 30ml was sequentially added 2 fluorobenzaldehyde 51b 0 01 mol urea 52 0 015 mol followed by catalytic amount of p Toluenesulfonic acid and refluxed at 70 75 C for 9 0 hr After completion of the reaction monitored by TLC the reaction mixture was treated with ice cold water The resulting solid product was filtered washed with water and purified by recrystallization from ethanol to furnish 53b Microwave method To a mixture of N 2 chloro 4 trifluoromethyl phenyl 3 oxobutanamide 50 0 01 mol 2 fluorobenzaldehyde 51b 0 01 mol urea 52 0 015 mol and catalytic amount of p Toluenesulfonic acid was added DMF 5 drops Reaction mixture was subjected to microwave irradiation for 7 5 min at 400 W On completion of the reaction monitored by TLC the reaction mixture was treated with ice cold water

The resulting solid product was filtered washed with water and purified by recrystallization from ethanol to give 53b IR KBr cm 1 3408 For NH 3064 For C H of Phenyl ring 1664 C O amide carbonyl stretching 1604 N H pyrimidine ring 1520 C C Phenyl ring stretching 1340 For C N C of pyrimidine 1065 C F stretching 665 C Cl stretching MS GC m z 428 Anal Cacd C 54 62 H 3 90 Cl 8 06 F 12 96 N 9 55 O 10 91 Obtained C 54 42 H 3 81 Cl 8 00 F 12 90 N 9 55 O 10 91 N 2 Chloro 4 trifluoromethyl phenyl 4 4 chlorophenyl 6 methyl 2 oxo 1 2 3 4 tetrahydropyrimidin 5 carboxamide 53c Conventional method To a solution of N 2 chloro 4 trifluoromethyl phenyl 3 oxobutanamide 50 0 01 mol in ethanol 30ml was sequentially added 4 chlorobenzaldehyde 51c 0 01 mol urea 52 0 015 mol followed by catalytic amount of p Toluenesulfonic acid and refluxed at 70 75 C for 10 0 hr After completion of the reaction monitored by TLC the reaction mixture was treated with ice cold water The resulting solid product was filtered washed with water and purified by recrystallization from ethanol to afford 53c Microwave method To a mixture of N 2 chloro 4 trifluoromethyl phenyl 3 oxobutanamide 50 0 01 mol 4 chlorobenzaldehyde 51c 0 01 mol urea 52 0 015 mol and a catalytic amount of p Toluenesulfonic acid was added DMF 10drops Reaction mixture was subjected to microwave irradiation for 8 5 min at 400 W After completion of reaction monitored by TLC the contents were poured into crushed ice The solid thus obtained was separated by filtration and purified by recrystallization from ethanol to produce 53c IR KBr cm 1 3387 For NH 3058 For C H of Phenyl ring 1668 C O amide carbonyl stretching 1607 N H pyrimidine ring 1528 C C Phenyl ring stretching 1344 For C N C of pyrimidine 1061 C F stretching 669 C Cl stretching MS GC m z 445 M Anal Cacd C 51 37 H 3 18 Cl 15 96 F 12 83 N 9 46 O 7 20 Found C 51 20 H 3 03 Cl 15 56 F 12 66 N 9 22 O 7 10



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