Thionyl Chloride → 1-Methyl-1H-pyrrole-2-carbonyl chloride

HRID 251891

Reaction equation

HRID 251891 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[C:7]([OH:9])=O.S(Cl)([Cl:12])=O>CCCCCC>[CH3:1][N:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[C:7]([Cl:12])=[O:9]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 814531-Methyl-2-pyrrolecarboxylic acid

Product 1

HCID 27950921-Methyl-1H-pyrrole-2-carbonyl chlorideYield 93.9%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

A mixture of 0.13 g of 1-methyl-1H-pyrrole-2-carboxylic acid, 0.15 g of thionyl chloride and 5 ml of hexane was heated under reflux for 2 hours. The reaction mixture was concentrated under reduced pressure to obtain 0.14 g of 1-methyl-1H-pyrrole-2-carbonyl chloride. To a mixture of 0.22 g of N-(2-aminobenzoyl)-N′-ethoxycarbonylhydrazine and 10 ml of pyridine was added 0.14 g of the resulting 1-methyl-1H-pyrrole-2-carbonyl chloride, and the mixture was stirred at room temperature for 2 hours. Water was poured into the reaction mixture, and a deposited precipitate was collected by filtration to obtain 0.11 g of the present compound (2) of the formula:

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hours
  3. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-7c918f6f8a314a2fa391db9e8de1f2d4
Source dataset
uspto-grants-2011_01
Patent number
US07867949B2

Linked notes

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