Water → N-(3-ethynylphenyl)acetamide

HRID 506583Notes

Reaction equation

HRID 506583 reaction equation
C(O[C:5](=[O:7])[CH3:6])(=O)C.[C:8]([C:10]1[CH:11]=[C:12]([CH:14]=[CH:15][CH:16]=1)[NH2:13])#[CH:9].O>CN(C)C1C=CN=CC=1.O1CCCC1>[C:5]([NH:13][C:12]1[CH:11]=[C:10]([C:8]#[CH:9])[CH:16]=[CH:15][CH:14]=1)(=[O:7])[CH3:6]

Participants

6

Reactant 3

HCID 962WaterHCID 7918Acetic AnhydrideHCID 104682Benzenamine, 3-ethynyl-

Product 1

HCID 2726447N-(3-ethynylphenyl)acetamideYield 96%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Acetic anhydride (13.8 mL, 144 mmol) was added dropwise to a solution of 3-ethynylaniline (14.0 g, 120 mmol) and 4-(Dimethylamino-)pyridine (DMAP) (1.5 g, 12 mmol) in tetrahydrofuran (300 mL). The mixture was stirred at room temperature for 2 hours, water (100 mL) was added to the mixture and the whole was extracted with dichloromethane (2×250 mL). The combined organics was washed with 10% citric acid (100 mL) followed by saturated sodium bicarbonate solution (100 mL), dried over MgSO4, filtered and concentrated in vacuo to afford 3-(acetylamino)phenylacetylene as a yellow solid (18.3 g, 96%).

Workup

  1. extractionthe whole was extracted with dichloromethane (2×250 mL)
  2. washThe combined organics was washed with 10% citric acid (100 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-614c3277ffb04b51840bda9259049b7b
Source dataset
uspto-grants-2010_08
Patent number
US07786113B2

Reaction notes

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