Triethylamine → HCID 58807441, compound

HRID 424298Notes

Reaction equation

HRID 424298 reaction equation
[NH2:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][P:7](=[O:14])([O:11][CH2:12][CH3:13])[O:8][CH2:9][CH3:10])=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:24](Cl)(=[O:27])[CH:25]=[CH2:26]>C1(C)C=CC=CC=1>[C:24]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][P:7](=[O:14])([O:8][CH2:9][CH3:10])[O:11][CH2:12][CH3:13])=[CH:15][CH:16]=1)(=[O:27])[CH:25]=[CH2:26]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 88358Diethyl p-aminobenzylphosphonate

Product 1

HCID 58807441HCID 58807441, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent3×

Procedure

To a solution of diethyl 4-(amino)benzylphosphonate (2.02 g; 8.3 mmoles) and triethylamine (1.02 g; 9 mmoles) in toluene (7 ml) cooled to 0-5° C., is added dropwise a solution of acryloyl chloride (0.91 g of 95% purity; 10 mmoles) in toluene (2 ml) for 30 min. Thereafter, more toluene (5 ml) is poured into the flask and the mixture is stirred at room temperature for two more hours. The reaction is terminated by addition of water (10 ml). The organic phase is extracted with diethyl ether, dried over MgSO4 and stripped of solvent under vacuum to afford a pale-yellow solid (2.22 g; yield 90%).

Workup

  1. customThe reaction is terminated by addition of water (10 ml)
  2. extractionThe organic phase is extracted with diethyl ether
  3. dry with materialdried over MgSO4
  4. customto afford a pale-yellow solid (2.22 g; yield 90%)

Sources & evidence

ORD record
ord-974c812269d5453ca561c2f7398b0c04
Source dataset
uspto-grants-2012_01
Patent number
US08105689B2

Reaction notes

Loading…