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

HRID 231491Notes

Reaction equation

HRID 231491 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[S:11][CH:10]=[C:9]([C:12]([OH:14])=O)[C:8]=2[CH:15]=1)([O-:3])=[O:2].S(Cl)(Cl)=O.CN(C=O)C.[CH2:25]([NH:28][CH2:29][CH2:30][CH3:31])[CH2:26][CH3:27]>ClC(Cl)(Cl)C.ClCCl>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[S:11][CH:10]=[C:9]([C:12]([N:28]([CH2:29][CH2:30][CH3:31])[CH2:25][CH2:26][CH3:27])=[O:14])[C:8]=2[CH:15]=1)([O-:3])=[O:2]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 8902DipropylamineHCID 24386Thionyl ChlorideHCID 235048365-Nitro-benzo[b]thiophene-3-carboxylic acid

Product 1

HCID 571746595-Nitro-N,N-dipropyl-3-benzothiophencarboxamide

Reagents, catalysts & solvents 2

HCID 62781,1,1-TrichloroethaneSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
30 °C

Procedure

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.

Workup

  1. temperatureThe mixture was refluxed for 2 hours
  2. customresulting in a clear solution
  3. customThe solvents were evaporated
  4. customwas removed by evaporation twice with toluene
  5. customThe crystalline product thus obtained
  6. washeluted through 200 g of silica gel with 1500 ml of a mixture (1:1) of dichloromethane and ethyl acetate
  7. washThe organic phase was washed with water
  8. dry with materialdried (MgSO4)
  9. customevaporated
  10. addition200 ml of n-heptane were added
  11. filtrationthe crystalline product filtered off

Sources & evidence

ORD record
ord-9dc25fe8b92e445a965172b7eaa95678
Source dataset
uspto-grants-1989_07
Patent number
US04847254

Reaction notes

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