Hydrochloric Acid → Ethyl dodecanoyl-3, 5-dimethylpyrrole-2-carboxylate

HRID 382821Notes

Reaction equation

HRID 382821 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].[CH3:5][C:6]1[CH:10]=[C:9]([CH3:11])[NH:8][C:7]=1[C:12]([O:14][CH2:15][CH3:16])=[O:13].[C:17](Cl)(=[O:29])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28].Cl>O.ClCCl>[C:17]([C:10]1[C:6]([CH3:5])=[C:7]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[NH:8][C:9]=1[CH3:11])(=[O:29])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8166Dodecanoyl chlorideHCID 1374771H-Pyrrole-2-carboxylic acid, 3,5-dimethyl-, ethyl esterHCID 6451240Aluminum(III) Chloride

Product 1

HCID 18362055Ethyl dodecanoyl-3, 5-dimethylpyrrole-2-carboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

1.46 g (11 mmol) of AlCl3 were added to a solution of 1.67 g (10 mmol) of ethyl 3,5-dimethylpyrrole-2-carboxylate a 2.63 g (12 mmol) of dodecanoyl chloride in 30 ml of absol. Dichloromethane and then stirred for 24 h. Addition of water and dilute HCl is followed by extraction twice with CH2Cl2. The organic phases are washed with dilute NaOH, dried over Na2SO4 and concentrated. The product is recrystallized from isopropanol.

Workup

  1. extractionis followed by extraction twice with CH2Cl2
  2. washThe organic phases are washed with dilute NaOH
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe product is recrystallized from isopropanol

Sources & evidence

ORD record
ord-85823facb44a4b2297b82673efd223d8
Source dataset
uspto-grants-2001_10
Patent number
US06310217B1

Reaction notes

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