Benzoyl chloride → Benzamide, N-2-propynyl-

HRID 2377279Notes

Reaction equation

HRID 2377279 reaction equation
[CH2:1]([NH2:4])[C:2]#[CH:3].C(N(CC)CC)C.[C:12](Cl)(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>ClCCl>[CH2:1]([NH:4][C:12](=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:2]#[CH:3]

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 239041Propargylamine

Product 1

HCID 5020678Benzamide, N-2-propynyl-

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of propargylamine (6 g, 109 mmol) and triethylamine (15 mL, 109 mmol) in dichloromethane (125 mL) was added dropwise benzoyl chloride (10.5 mL, 90 mmol) at about 0° C. The ice-bath was removed and stirring was continued for about 30 min. Then the reaction mixture was concentrated under vacuum, the residue was diluted with water and was extracted with ethyl acetate. The combined organic extracts were dried (MgSO4), filtered and concentrated under vacuum to provide Example 643. MS (APCI): m/z 160 (M+H)+.

Workup

  1. customThe ice-bath was removed
  2. concentrationThen the reaction mixture was concentrated under vacuum
  3. additionthe residue was diluted with water
  4. extractionwas extracted with ethyl acetate
  5. dry with materialThe combined organic extracts were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum
  8. customto provide Example 643

Sources & evidence

ORD record
ord-a2ed4b02ead74039a148f471ec04ec00
Source dataset
uspto-grants-2008_12
Patent number
US07468371B2

Reaction notes

Loading…