Triethylamine → HCID 22632759, compound

HRID 2416621Notes

Reaction equation

HRID 2416621 reaction equation
[C:1]1([C:7]2[O:8][CH:9]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:10](=[O:13])[NH:11][N:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:20]1(OB(O)O)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(N(CC)CC)C>C(Cl)Cl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[C:1]1([C:7]2[O:8][CH:9]([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:10](=[O:13])[N:11]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[N:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 78412Phenyl dihydrogen orthoborateHCID 22632809HCID 22632809, compound

Product 1

HCID 22632759HCID 22632759, compoundYield 37%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 2,6-diphenyl-4H-1,3,4-oxadiazine-5-one (0.1 g), phenyl boric acid (0.13 g), copper acetate (0.18 g) and triethylamine (0.12 g) was stirred vigorously in methylene chloride (15 ml) overnight at room temperature. The reaction in solution was purified directly by silica gel chromatography (ethyl acetate/hexane, 1:2), to give the title compound as a white powder (0.048 g, 37%).

Workup

  1. customThe reaction in solution
  2. customwas purified directly by silica gel chromatography (ethyl acetate/hexane, 1:2)

Sources & evidence

ORD record
ord-ad222466ce714db6908d9372caae192d
Source dataset
uspto-grants-2004_11
Patent number
US06825192B1

Reaction notes

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