Sulfanilamide → ethyl 5-(4-bromophenyl)-2-methyl-1-(4-sulfamoylphenyl)-1H-pyrrole-3-carboxylate

HRID 18640

Reaction equation

HRID 18640 reaction equation
[C:1]([CH:4]([CH2:10][C:11]([C:13]1[CH:18]=[CH:17][C:16]([Br:19])=[CH:15][CH:14]=1)=O)[C:5]([O:7][CH2:8][CH3:9])=[O:6])(=O)[CH3:2].[NH2:20][C:21]1[CH:26]=[CH:25][C:24]([S:27]([NH2:30])(=[O:29])=[O:28])=[CH:23][CH:22]=1>C(O)(=O)C>[NH2:30][S:27]([C:24]1[CH:23]=[CH:22][C:21]([N:20]2[C:11]([C:13]3[CH:18]=[CH:17][C:16]([Br:19])=[CH:15][CH:14]=3)=[CH:10][C:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])=[C:1]2[CH3:2])=[CH:26][CH:25]=1)(=[O:28])=[O:29]

Participants

4

Reactant 2

HCID 5333SulfanilamideHCID 14173974Ethyl 2-acetyl-4-(4-bromophenyl)-4-oxobutanoate

Product 1

HCID 24895703ethyl 5-(4-bromophenyl)-2-methyl-1-(4-sulfamoylphenyl)-1H-pyrrole-3-carboxylate

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of Example 1A (3.3 g, 10.1 mmol) and 4-aminobenzenesulfonamide (1.74 g, 10.1 mmol) in glacial acetic acid (75 mL) was heated to 100° C. for 48 hours. After cooling the mixture was concentrated under reduced pressure. Ether (50 mL) was added to the residue and the precipitate was isolated by filtration. The pale yellow solid was washed with ether and dried. 1H NMR (CDCl3) δ ppm 1.32 (3H), 2.20 (3H), 3.50 (2H), 4.27 (2H), 6.85 (1H), 7.30-7.90 (8H); MS (ESI) m/z m/z 462/464.

Workup

  1. temperatureAfter cooling the mixture
  2. concentrationwas concentrated under reduced pressure
  3. additionEther (50 mL) was added to the residue
  4. customthe precipitate was isolated by filtration
  5. washThe pale yellow solid was washed with ether
  6. customdried

Sources & evidence

ORD record
ord-26b8734ec46f438d851b80c723a17934
Source dataset
uspto-grants-2010_06
Patent number
US07741364B2

Linked notes

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