4-Chloroaniline → N-[[(4-chlorophenyl)amino]carbonyl]-5-ethyl-2-pyrrolesulfonamide

HRID 1464135Notes

Reaction equation

HRID 1464135 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.Cl[S:10]([N:13]=[C:14]=[O:15])(=[O:12])=[O:11].[CH2:16]([C:18]1[NH:19][CH:20]=[CH:21][CH:22]=1)[CH3:17]>O1CCCC1>[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:14]([NH:13][S:10]([C:20]2[NH:19][C:18]([CH2:16][CH3:17])=[CH:22][CH:21]=2)(=[O:12])=[O:11])=[O:15])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 78124-ChloroanilineHCID 70918Chlorosulfonyl isocyanateHCID 1370752-Ethylpyrrole

Product 1

HCID 15669332N-[[(4-chlorophenyl)amino]carbonyl]-5-ethyl-2-pyrrolesulfonamideYield 5.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

4-Chloroaniline (4.5 g, 35.4 mmole) was combined with tetrahydrofuran (80 ml) under nitrogen and cooled to -78° C. Chlorosulfonyl isocyanate (3.0 ml, 35.4 mmole) was added and the mixture stirred 1 hour at -78° C. 2-Ethylpyrrole (3.66 g, 38.9 mmole) was added and the mixture allowed to warm to room temperature and then stirred for 2 hours. The reaction was quenched with water and then concentrated. The residue was dissolved in methylene chloride (100 ml) which was extracted with three 100 ml portions of aqueous NaOH. The aqueous layer was acidifed and extracted with methylene chloride. The organic layers were combined and washed with two 100 ml portions of water. The organic layer was then dried over Na2SO4, filtered and concentrated. The resulting dark oil was flashed chromatographed over silica eluding with 4% methanol/methylene chloride. Removal of solvent provided 0.64 g of product.

Workup

  1. temperatureto warm to room temperature
  2. stirringstirred for 2 hours
  3. customThe reaction was quenched with water
  4. concentrationconcentrated
  5. dissolutionThe residue was dissolved in methylene chloride (100 ml) which
  6. extractionwas extracted with three 100 ml portions of aqueous NaOH
  7. extractionextracted with methylene chloride
  8. washwashed with two 100 ml portions of water
  9. dry with materialThe organic layer was then dried over Na2SO4
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customThe resulting dark oil was flashed chromatographed over silica eluding with 4% methanol/methylene chloride
  13. customRemoval of solvent

Sources & evidence

ORD record
ord-fc5238e370f14ed38b14cd1beb566f60
Source dataset
uspto-grants-1994_04
Patent number
US05302724

Reaction notes

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