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

HRID 334601Notes

Reaction equation

HRID 334601 reaction equation
[Cl-].[C:2]([OH:8])(=O)[CH2:3][CH2:4][C:5]#[CH:6].[Cl:9][C:10]1[CH:11]=[C:12]([NH:16][CH3:17])[CH:13]=[CH:14][CH:15]=1>C(Cl)Cl>[Cl:9][C:10]1[CH:11]=[C:12]([N:16]([CH3:17])[C:2](=[O:8])[CH2:3][CH2:4][C:5]#[CH:6])[CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 312ChlorideHCID 224644-Pentynoic acidHCID 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

Oxayl 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-43881576710a4a658cf048c334ea3439
Source dataset
uspto-grants-2014_11
Patent number
US08883826B2

Reaction notes

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