Triethylamine → HCID 19890950, compound

HRID 893632Notes

Reaction equation

HRID 893632 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][Se:8][C:9]1[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=1[C:11]([OH:13])=O.O=C1N(P(Cl)(N2CCOC2=O)=O)CCO1.[NH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][N:35]=1.C(N(CC)CC)C>ClCCl.C(OCC)C>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][Se:8][C:9]1[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=1[C:11]([NH:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][N:35]=1)=[O:13]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 104392-AminopyridineHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 19890937HCID 19890937, compound

Product 1

HCID 19890950HCID 19890950, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 5.84 g (0.02 mol) 2-(2-picolylseleno)benzoic acid (from Example 1) in 40 ml dichloromethane that has been cooled to 0° C. are added in one portion 5 g (0.02 mol) bis[2-oxo-3-oxazolidinyl]phosphoryl chloride. After stirring for 2 hours at room temperature 1.88 g (0.02 mol) 2-aminopyridine, 50 ml dichloromethane and 6.4 ml triethylamine are added dropwise in succession at 10° C. and stirring is continued at room temperature for 20 h. The reaction mixture is extracted twice with 100 ml portions of water, dried over sodium sulfate and the solvent removed. The brown oil (7 g) is taken up in 100 ml 1 N HCl, filtered, the filtrate basified with 13 ml 10 N sodium hydroxide and extracted with 100 ml ethyl acetate. The organic phase is dried, concentrated and the solid residue obtained is stirred for 48 h with 100 ml diethyl ether. After filtration the crude product is cleaned up by column chromatography (silica gel/dichloromethane) and recrystallized from 20 ml 2-propanol.

Workup

  1. additionare added dropwise in succession at 10° C.
  2. extractionThe reaction mixture is extracted twice with 100 ml portions of water
  3. dry with materialdried over sodium sulfate
  4. customthe solvent removed
  5. filtrationfiltered
  6. extractionextracted with 100 ml ethyl acetate
  7. customThe organic phase is dried
  8. concentrationconcentrated
  9. customthe solid residue obtained
  10. filtrationAfter filtration the crude product
  11. customrecrystallized from 20 ml 2-propanol

Sources & evidence

ORD record
ord-d45f86637ba3441e90aa75772d360b0a
Source dataset
uspto-grants-1992_06
Patent number
US05126357

Reaction notes

Loading…