Oxalyl chloride → 5-(3,3,3-trifluoropropyl)-1H-pyrrole-2-carboxylic acid chloride

HRID 397964Notes

Reaction equation

HRID 397964 reaction equation
[F:1][C:2]([F:14])([F:13])[CH2:3][CH2:4][C:5]1[NH:9][C:8]([C:10](O)=[O:11])=[CH:7][CH:6]=1.C(Cl)(=O)C([Cl:18])=O>C(Cl)Cl.CN(C=O)C>[F:1][C:2]([F:14])([F:13])[CH2:3][CH2:4][C:5]1[NH:9][C:8]([C:10]([Cl:18])=[O:11])=[CH:7][CH:6]=1

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 225072695-(3,3,3-trifluoropropyl)-1H-pyrrole-2-carboxylic acid

Product 1

HCID 879771705-(3,3,3-trifluoropropyl)-1H-pyrrole-2-carboxylic acid chlorideYield 83.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

5-(3,3,3-trifluoropropyl)-1H-pyrrole-2-carboxylic acid (5.55 mmol, 1.15 g) in CH2Cl2 (10 ml) was treated with oxalyl chloride (16.7 mmol, 1.5 ml), then DMF (1 drop). The solution was heated to reflux for 1 h, then concentrated under reduced pressure to provide 5-(3,3,3-trifluoropropyl)-1H-pyrrole-2-carboxylic acid chloride (1.04 g). 1H NMR (CDCl3) δ10.25 (1H, br s), 7.12 (1H, dd, J=4.0, 2.6), 6.12 (1H, dd, J=3.8, 2.7), 3.05-2.88 (2H, m), 2.59-2.41 (2H, m).

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux for 1 h
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-fbe29452089d42e98c507786f7ee3141
Source dataset
uspto-grants-2003_08
Patent number
US06610730B2

Reaction notes

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