Azobisisobutyronitrile → Ethyl 4-(bromomethyl)-5-(4-chlorophenyl)-3-(4-sulfamoylphenyl)thiophene-2-carboxylate

HRID 1053262Notes

Reaction equation

HRID 1053262 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[S:7][C:8]([C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=2)=[C:9]([CH3:21])[C:10]=1[C:11]1[CH:16]=[CH:15][C:14]([S:17](=[O:20])(=[O:19])[NH2:18])=[CH:13][CH:12]=1)=[O:5])[CH3:2].C1C(=O)N([Br:36])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C>ClC1C=CC=CC=1>[Br:36][CH2:21][C:9]1[C:10]([C:11]2[CH:12]=[CH:13][C:14]([S:17](=[O:20])(=[O:19])[NH2:18])=[CH:15][CH:16]=2)=[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[S:7][C:8]=1[C:22]1[CH:23]=[CH:24][C:25]([Cl:28])=[CH:26][CH:27]=1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 68285835Ethyl-5-(4-chlorophenyl)-4-methyl-3-(4-sulfamoylphenyl)thiophene-2-carboxylate2×

Product 1

HCID 68285313Ethyl 4-(bromomethyl)-5-(4-chlorophenyl)-3-(4-sulfamoylphenyl)thiophene-2-carboxylateYield 59.32%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Conditions

Temperature
85 °C

Procedure

To a stirred solution of Ethyl 5-(4-chlorophenyl)-4-methyl-3-(4-sulfamoylphenyl)thiophene-2-carboxylate (Compound 1b, 4.0 g, 9.17 mmol) in chlorobenzene (50 ml) were added NBS (1.77 g, 10.09 mmol) and AIBN (1.65 g, 10.09 mmol) at 25° C. The reaction mixture was then stirred at 85° C. for 4 hr. The progress of the reaction was monitored by TLC. The reaction mixture was then cooled to room temperature and was quenched in aqueous sodium chloride solution (50 ml). The mixture so obtained was then extracted with Ethyl acetate (2×50 ml). The organic layer was washed with brine (1×50 ml) and dried over sodium sulfate and concentrated under reduced pressure to obtain crude product (4.0 g). The crude product was then purified by column chromatography over silica gel (100-200 mesh) using 40% ethyl acetate in hexanes as an eluent to obtain the title compound (2.8 g, 59.32%).

Workup

  1. temperatureThe reaction mixture was then cooled to room temperature
  2. customwas quenched in aqueous sodium chloride solution (50 ml)
  3. customThe mixture so obtained
  4. extractionwas then extracted with Ethyl acetate (2×50 ml)
  5. washThe organic layer was washed with brine (1×50 ml)
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customto obtain crude product (4.0 g)
  9. customThe crude product was then purified by column chromatography over silica gel (100-200 mesh)

Sources & evidence

ORD record
ord-eff635d13d7540218aca3d200cfcf414
Source dataset
uspto-grants-2016_07
Patent number
US09393247B2

Reaction notes

Loading…