1,2-Dichloroethane → 5-(4-chlorophenyl)-N,N,1,4-tetramethyl-3-(4-sulfamoylphenyl)-1H-pyrrole-2-carboxamide

HRID 1053307Notes

Reaction equation

HRID 1053307 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH3:13])[C:11]([C:14](O)=[O:15])=[C:10]([C:17]3[CH:22]=[CH:21][C:20]([S:23](=[O:26])(=[O:25])[NH2:24])=[CH:19][CH:18]=3)[C:9]=2[CH3:27])=[CH:4][CH:3]=1.C1C=CC2N(O)N=NC=2C=1.Cl.[CH3:39][NH:40][CH3:41].C(Cl)CCl.C(N(CC)CC)C>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:12]([CH3:13])[C:11]([C:14]([N:40]([CH3:41])[CH3:39])=[O:15])=[C:10]([C:17]3[CH:22]=[CH:21][C:20]([S:23](=[O:26])(=[O:25])[NH2:24])=[CH:19][CH:18]=3)[C:9]=2[CH3:27])=[CH:6][CH:7]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 757711-HydroxybenzotriazoleHCID 709126865-(4-chlorophenyl)-1,4-dimethyl-3-(4-sulfamoylphenyl)-1H-pyrrole-2-carboxylic acid

Product 1

HCID 601693505-(4-chlorophenyl)-N,N,1,4-tetramethyl-3-(4-sulfamoylphenyl)-1H-pyrrole-2-carboxamideYield 88.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 5-(4-chlorophenyl)-1,4-dimethyl-3-(4-sulfamoylphenyl)-1H-pyrrole-2-carboxylic acid (49ε, 1.00 g, 2.47 mmol) in DMF (15 ml) was added HOBT (0.41 g, 2.72 mmol) at room temperature, which was then followed by the addition of dimethylamine hydrochloride (0.40 g, 4.94 mmol). the reaction mixture was cooled to 0° C. and to the cooled reaction mixture was then added EDC (0.71 g, 3.70 mmol) and triethylamine (1.00 g, 1.37 ml, 9.88 mmol). The reaction mixture was then stirred at room temperature for 16 hours. The progress of the reaction was monitored by TLC. The reaction mixture was then concentrated under reduced pressure. Ethyl acetate (100 ml) was added to the residue so obtained. The mixture so obtained was then washed with saturated sodium bicarbonate solution (20 ml) followed by washing with brine (20 ml). The organic layer obtained was dried over anhydrous sodium sulphate. The dried organic layer was then concentrated under reduced pressure to obtain a crude product. The crude product was purified by column chromatography over silica gel (100-200 mesh) using 90% ethyl acetate in hexanes as an eluent to obtain the title compound (0.94 g, 88.1%).

Workup

  1. concentrationThe reaction mixture was then concentrated under reduced pressure
  2. additionEthyl acetate (100 ml) was added to the residue
  3. customso obtained
  4. customThe mixture so obtained
  5. washwas then washed with saturated sodium bicarbonate solution (20 ml)
  6. washby washing with brine (20 ml)
  7. customThe organic layer obtained
  8. dry with materialwas dried over anhydrous sodium sulphate
  9. concentrationThe dried organic layer was then concentrated under reduced pressure
  10. customto obtain a crude product
  11. customThe crude product was purified by column chromatography over silica gel (100-200 mesh)

Sources & evidence

ORD record
ord-c26486cd874a46aeb470054ab344a722
Source dataset
uspto-grants-2016_07
Patent number
US09393247B2

Reaction notes

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