Triethylamine → 4-Bromo-N-(prop-2-yn-1-yl)benzamide

HRID 976434Notes

Reaction equation

HRID 976434 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.[CH2:11]([NH2:14])[C:12]#[CH:13].C(N(CC)CC)C.C(OCC)(=O)C>ClCCl>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:14][CH2:11][C:12]#[CH:13])=[O:7])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 685154-Bromobenzoyl chlorideHCID 239041Propargylamine

Product 1

HCID 1873244-Bromo-N-(prop-2-yn-1-yl)benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 4-bromobenzoyl chloride (4.39 g, 20 mmol) in 40 mL dichloromethane at 0° C., propargylamine (1.10 g, 20 mmol) was added, followed by triethylamine (4.05 g, 40 mmol). The mixture was stirred at room temperature for 40 minutes. 150 mL ethyl acetate was added and filtered. The filtrate was washed with 2×40 mL water and 40 mL brine, dried and concentrated to give 4-Bromo-N-(2-propynyl)benzamide. 4-Bromo-N-(2-propynyl)benzamide was added into ice cooled 47 mL concentrated sulfuric acid. The reaction was stirred at 5°-10° C. for 3 hours and at room temperature overnight. The mixture was poured into 500 mL ice water, neutralized with sodium carbonate to pH 8 and extracted with 3×250 mL ethyl acetate. The combined organic extracts were washed with 200 mL water and 100 mL brine, dried and concentrated to afford compound A (4.5 g, 95%) as a light yellow solid.

Workup

  1. filtrationfiltered
  2. washThe filtrate was washed with 2×40 mL water and 40 mL brine
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-4a0e800247534f8ca0338b023a70dc84
Source dataset
uspto-grants-1997_03
Patent number
US05612359

Reaction notes

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