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

HRID 1913384

Reaction equation

HRID 1913384 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-d7b6c2cac3e140ceafc67beaafe23674
Source dataset
uspto-grants-2013_12
Patent number
US08609713B2

Linked notes

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