Diethylamine → Acetamide, 2-[(2-bromo-3-pyridinyl)oxy]-N,N-diethyl-

HRID 1649787Notes

Reaction equation

HRID 1649787 reaction equation
[CH2:1]([NH:3][CH2:4][CH3:5])[CH3:2].[Br:6][C:7]1[C:12]([O:13][CH2:14][C:15]([OH:17])=O)=[CH:11][CH:10]=[CH:9][N:8]=1.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1.O>[Br:6][C:7]1[C:12]([O:13][CH2:14][C:15]([N:3]([CH2:4][CH3:5])[CH2:1][CH3:2])=[O:17])=[CH:11][CH:10]=[CH:9][N:8]=1

Participants

7

Reactant 4

HCID 8021Diethylamine2×HCID 14812Phosphorus oxide (P4O10)HCID 516892Sodium BicarbonateHCID 19854782[(2-Bromopyridin-3-yl)oxy]acetic acid

Product 1

HCID 19854819Acetamide, 2-[(2-bromo-3-pyridinyl)oxy]-N,N-diethyl-Yield 87.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent2×

Procedure

Diethylamine (0.874 g) was slowly added with cooling to [(2-bromo-3-pyridinyl)oxy]acetic acid (2.58 g) in toluene (10 ml). The solution was then dded to phosphorous pentoxide (1.87 g) and diethylamine (1.74 g) in toluene (10 ml). After the addition the mixture was heated under reflux overnight. The dark solution was diluted with water (20 ml), made alkaline with 8% sodium bicarbonate (20 ml) and extracted with ethyl acetate (3×30 ml). The combined organic extracts were dried and the solvent was evaporated in vacuo to give the title compound as a brown oil (2.8 g). t.l.c. (toluene-ethanol-0.88 ammonia 80:20:1) Rf 0.47.

Workup

  1. additionAfter the addition the mixture
  2. temperaturewas heated
  3. temperatureunder reflux overnight
  4. extractionextracted with ethyl acetate (3×30 ml)
  5. customThe combined organic extracts were dried
  6. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-8764ee847a6642078a5cda1ad1e83a85
Source dataset
uspto-grants-1990_05
Patent number
US04921867

Reaction notes

Loading…