تفاعل #318673

معادلة التفاعل

5-nitro-3-benzothiophencarboxylic acid

thionyl chloride

DMF

dipropylamine

→

5-Nitro-N,N-dipropyl-3-benzothiophencarboxamide

المذيبات

dichloromethane

1,1,1-trichloroethane

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe mixture was refluxed for 2 hours
2. 2
   أخرىresulting in a clear solution
3. 3
   أخرىThe solvents were evaporated
4. 4
   أخرىwas removed by evaporation twice with toluene
5. 5
   أخرىThe crystalline product thus obtained
6. 6
   غسيلeluted through 200 g of silica gel with 1500 ml of a mixture (1:1) of dichloromethane and ethyl acetate
7. 7
   غسيلThe organic phase was washed with water
8. 8
   تجفيفdried (MgSO4)
9. 9
   أخرىevaporated
10. 10
    workup.ADDITION200 ml of n-heptane were added
11. 11
    ترشيحthe crystalline product filtered off

الإجراء التجريبي

45 g of 5-nitro-3-benzothiophencarboxylic acid were suspended in 150 ml of 1,1,1-trichloroethane. 100 ml of thionyl chloride and 0.5 ml of DMF were added. The mixture was refluxed for 2 hours resulting in a clear solution. The solvents were evaporated and remaining thionyl chloride was removed by evaporation twice with toluene. The crystalline product thus obtained was added in small portions to a solution of 60 g of dipropylamine in 500 ml of dichloromethane below 10° C. The mixture was heated to 30° C. and eluted through 200 g of silica gel with 1500 ml of a mixture (1:1) of dichloromethane and ethyl acetate. The organic phase was washed with water, dried (MgSO4) and evaporated. 200 ml of n-heptane were added and the crystalline product filtered off. Yield: 56 g. M.P. 100° C.

المصدر