Triethylamine → HCID 14460584, compound

HRID 1084805Notes

Reaction equation

[CH3:1][N:2]([CH3:12])[C:3]1[CH:11]=[CH:10][C:6]([CH:7]=[N:8][OH:9])=[CH:5][CH:4]=1.ClN1C(=O)CCC1=O.[CH:21]([P:23](=[O:28])([O:26][CH3:27])[O:24][CH3:25])=[CH2:22].C(N(CC)CC)C>>[CH3:1][N:2]([CH3:12])[C:3]1[CH:11]=[CH:10][C:6]([C:7]2[CH2:22][CH:21]([P:23](=[O:28])([O:26][CH3:27])[O:24][CH3:25])[O:9][N:8]=2)=[CH:5][CH:4]=1

Participants

Reactant 4

HCID 8471Triethylamine

HCID 31398Chlorosuccinimide

HCID 78376Dimethyl vinylphosphonate

HCID 351532HCID 351532, compound

Product 1

HCID 14460584HCID 14460584, compoundYield 46.7%

Procedure

In analogy to Example 1, 40 g (0.24 mol) of 4-dimethylaminobenzaldoxime, 36.17 g (0.27 mol) of N-chlorosuccinimide, 32.7 g (0.24 mol) of dimethyl vinylphosphonate and 52.3 ml (0.376 mol) of triethylamine are reacted. The resulting oily crude product is purified by chromatography on silica gel and recrystallization from tert.butyl methyl ether. 33.4 g of the isoxazoline of melting point 123° C. (decomposition) are obtained.

Workup

customThe resulting oily crude product is purified by chromatography on silica gel and recrystallization from tert.butyl methyl ether

Sources & evidence

ORD record: ord-88d8bc59cb554dcca18840991773eecd
Source dataset: uspto-grants-1991_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05006515

Reaction notes

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