Triethylamine → HCID 57467435, compound

HRID 1890778Notes

Reaction equation

HRID 1890778 reaction equation
[CH3:1][C:2]([O:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([CH3:6])[C:3]([NH2:5])=O.C(N(CC)CC)C.FC(F)(F)C(OC(=O)C(F)(F)F)=O>C(Cl)Cl>[CH3:6][C:2]([O:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([CH3:1])[C:3]#[N:5]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 123215122-Methyl-2-phenoxypropanamide

Product 1

HCID 57467435HCID 57467435, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-methyl-2-phenoxypropanamide from Step C (0.01 mol) in dry CH2Cl2 (50 mL) and triethylamine (3.03 g, 0.03 mol) at 0° C. was added trifluoroacetic anhydride (3.15 g, 0.015 mol). After the addition was complete, the solution was allowed to warm to room temperature and stirring was continued at ambient temperature overnight. The reaction mixture was then refluxed for 3 hours. After cooling to room temperature and dilution with CH2Cl2 (100 mL), the solution was washed with saturated aqueous NaHCO3 (50 mL×3), water, and brine and dried over sodium sulfated. Evaporation gave the titled compound. 1H NMR (400 MHz, CDCl3) δ ppm 7.32˜7.36 (m, 2H), 7.14˜7.20 (m, 3H), 1.71 (s, 6H).

Workup

  1. additionAfter the addition
  2. temperatureThe reaction mixture was then refluxed for 3 hours
  3. temperatureAfter cooling to room temperature
  4. washdilution with CH2Cl2 (100 mL), the solution was washed with saturated aqueous NaHCO3 (50 mL×3), water, and brine
  5. dry with materialdried over sodium
  6. customEvaporation

Sources & evidence

ORD record
ord-d06c4abb71ac42d49bfeee6ffa365b06
Source dataset
uspto-grants-2013_08
Patent number
US08507493B2

Reaction notes

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