Triethylamine → 3-(3-Pyridyl)acryloyl chloride hydrochloride

HRID 1968927Notes

Reaction equation

HRID 1968927 reaction equation
C(N(CC)CC)C.[N:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH:14]=[CH:15][C:16]([OH:18])=O)[CH:9]=1.C(Cl)(=O)C([Cl:22])=O>ClCCl>[ClH:22].[N:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH:14]=[CH:15][C:16]([Cl:22])=[O:18])[CH:9]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 1019843-(3-Pyridinyl)-2-propenoic acid

Product 1

HCID 713600273-(3-Pyridyl)acryloyl chloride hydrochloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (0.5 ml) was added dropwise to a suspension of 3-pyridin-3-ylacrylic acid (5.0 g) in anhydrous dichloromethane (30 ml), and 6 ml of oxalyl chloride was added dropwise slowly in an ice-bath with the temperature no more than 5° C. After addition, the reaction was carried out for 30 min in an ice-bath, and then at room temperature overnight. The completion of reaction was indicated by TLC. The reaction mixture was concentrated under reduced pressure to give a white solid, which was left to stand at room temperature for 1 h, and used directly for the next step.

Workup

  1. additionwas added dropwise slowly in an ice-bath with the temperature no more than 5° C
  2. additionAfter addition
  3. customat room temperature
  4. customovernight
  5. customThe completion of reaction
  6. concentrationThe reaction mixture was concentrated under reduced pressure
  7. customto give a white solid, which
  8. waitwas left
  9. waitto stand at room temperature for 1 h

Sources & evidence

ORD record
ord-8891fb6010e2448e96330da3c46f713f
Source dataset
uspto-grants-2013_04
Patent number
US08426446B2

Reaction notes

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