p-Toluenesulfonic acid → 1-(3-Dimethylaminophenyl)-5-methyl-2-phenyl-1H-pyrrole-3-carboxylic acid ethyl ester

HRID 413897

Reaction equation

HRID 413897 reaction equation
Cl.Cl.[CH3:3][N:4]([CH3:12])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([NH2:11])[CH:6]=1.[CH2:13]([O:15][C:16](=[O:30])[CH:17]([C:22](=O)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:18][C:19](=O)[CH3:20])[CH3:14].C(N(CC)CC)C.CC1C=CC(S(O)(=O)=O)=CC=1>C(O)C.C(Cl)Cl>[CH2:13]([O:15][C:16]([C:17]1[CH:18]=[C:19]([CH3:20])[N:11]([C:7]2[CH:8]=[CH:9][CH:10]=[C:5]([N:4]([CH3:12])[CH3:3])[CH:6]=2)[C:22]=1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:30])[CH3:14]

Participants

7

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 8471TriethylamineHCID 771241,3-Benzenediamine, N1,N1-dimethyl-, hydrochloride (1:2)HCID 14689358Ethyl 2-benzoyl-4-oxopentanoate

Product 1

HCID 101547861-(3-Dimethylaminophenyl)-5-methyl-2-phenyl-1H-pyrrole-3-carboxylic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

N,N-Dimethyl-1,3-phenylenediamine dihydrochloride (5 mmol, 1.0 g), 2-benzoyl-4-oxo-pentanoic acid ethyl ester (5 mmol, 1.2 g), triethylamine (10 mmol, 1.0 g), and tosic acid (0.1 g) were combined in ethanol, then heated under reflux. The resulting oil was resuspended in methylene chloride, then washed with water, 5% sodium bicarbonate, and brine. The organic layer was dried over NaSO4, then the solids were separated and the solvents removed under vacuum. The crude material was purified over silica gel and yielded the named product (m.p. 111.7° C.-114° C.).

Workup

  1. temperatureheated
  2. temperatureunder reflux
  3. washwashed with water, 5% sodium bicarbonate, and brine
  4. dry with materialThe organic layer was dried over NaSO4
  5. customthe solids were separated
  6. customthe solvents removed under vacuum
  7. customThe crude material was purified over silica gel

Sources & evidence

ORD record
ord-ea1930b113f54eb1b9d7b37a2fc12730
Source dataset
uspto-grants-2003_05
Patent number
US06569890B2

Linked notes

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