4-Pentynoic acid → Pent-4-ynoic acid (3-chloro-phenyl)-methyl-amide

HRID 422327Notes

Reaction equation

HRID 422327 reaction equation
C(Cl)(=O)C(Cl)=O.[C:7]([OH:13])(=O)[CH2:8][CH2:9][C:10]#[CH:11].[Cl:14][C:15]1[CH:16]=[C:17]([NH:21][CH3:22])[CH:18]=[CH:19][CH:20]=1>C(Cl)Cl>[Cl:14][C:15]1[CH:16]=[C:17]([N:21]([CH3:22])[C:7](=[O:13])[CH2:8][CH2:9][C:10]#[CH:11])[CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 224644-Pentynoic acidHCID 65578Oxalyl chlorideHCID 1389003-chloro-N-methylaniline

Product 1

HCID 86086853Pent-4-ynoic acid (3-chloro-phenyl)-methyl-amideYield 88.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

Oxalyl chloride (89 μL, 1.02 mmol) was added to a solution of pent-4-ynoic acid (50 mg, 0.51 mmol) in DCM (3 mL). The reaction mixture was stirred at 50° C. for 1 hour, was cooled to 0° C. and was added dropwise to a solution of (3-chloro-phenyl)-methyl-amine (62 μL, 0.51 mmol). The reaction mixture was stirred for 2 hours at room temperature. After evaporation of the solvent, the crude residue was purified by flash chromatography (DCM/MeOH 99:1) to yield 100 mg (0.45 mmol, 88%) of pent-4-ynoic acid (3-chloro-phenyl)-methyl-amide.

Workup

  1. temperaturewas cooled to 0° C.
  2. stirringThe reaction mixture was stirred for 2 hours at room temperature
  3. customAfter evaporation of the solvent
  4. customthe crude residue was purified by flash chromatography (DCM/MeOH 99:1)

Sources & evidence

ORD record
ord-409991cdda4b4606bc49f4f22519e07e
Source dataset
uspto-grants-2012_01
Patent number
US08101637B2

Reaction notes

Loading…