Triethylamine → (3-Phenoxybenzoyl)amino-2-propyne

HRID 439414

Reaction equation

HRID 439414 reaction equation
[NH2:1][CH2:2][C:3]#[CH:4].C(N(CC)CC)C.[O:12]([C:19]1[CH:20]=[C:21]([CH:25]=[CH:26][CH:27]=1)[C:22](Cl)=[O:23])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>ClCCl>[O:12]([C:19]1[CH:20]=[C:21]([CH:25]=[CH:26][CH:27]=1)[C:22]([NH:1][CH2:2][C:3]#[CH:4])=[O:23])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 239041PropargylamineHCID 27603413-Phenoxybenzoyl chloride

Product 1

HCID 22411600(3-Phenoxybenzoyl)amino-2-propyneYield 74.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a dichloromethane (25 mL) solution of amino-2-propyne (0.96 g, 17.43 mmol) and triethylamine (3.33 mL, 23.7 mmol) at 0° C. was added 3-phenoxybenzoyl chloride (3.68 g, 15.8 mmol) in dichloromethane (25 mL) in a dropwise fashion. The reaction was stirred for 1 h after removing the cooling bath and partitioned between dichloromethane and 10% aqueous HCl. The layers were separated and the aqueous layer was extracted with dichloromethane (2×). The combined organic layers were washed (1×, saturated sodium bicarbonate; 1×, brine), dried (MgSO4), and concentrated under vacuum to give a golden oil. Recrystallization with ehter ethyl acetate provided the title compound as a colorless solid (2.95 g, 74%).

Workup

  1. customafter removing the cooling bath
  2. custompartitioned between dichloromethane and 10% aqueous HCl
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with dichloromethane (2×)
  5. washThe combined organic layers were washed (1×, saturated sodium bicarbonate; 1×, brine)
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated under vacuum
  8. customto give a golden oil
  9. customRecrystallization with ehter ethyl acetate

Sources & evidence

ORD record
ord-9b6da40b4f8d4c4587842a6f30a4effb
Source dataset
uspto-grants-1996_05
Patent number
US05514702

Linked notes

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