Triethylamine → Dimethyl 3(4-nitrophenyl)-2-isoxazolin-5-ylphosphonate

HRID 1084804Notes

Reaction equation

HRID 1084804 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([CH:8]=[N:9][OH:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].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>>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:8]2[CH2:22][CH:21]([P:23](=[O:28])([O:26][CH3:27])[O:24][CH3:25])[O:10][N:9]=2)=[CH:11][CH:12]=1)([O-:3])=[O:2]

Participants

5

Reactant 4

HCID 8471TriethylamineHCID 31398ChlorosuccinimideHCID 78376Dimethyl vinylphosphonateHCID 96339p-Nitrobenzaldoxime

Product 1

HCID 14460583Dimethyl 3(4-nitrophenyl)-2-isoxazolin-5-ylphosphonate

Procedure

Preparation is carried out in analogy to Example 1 from 19.6 g (0.118 mol) of 4-nitrobenzaldoxime, 17.4 g (0.13 mol) of N-chlorosuccinimide, 16.1 g (0.118 mol) of dimethyl vinylphosphonate and 18.7 ml (0.13 mol) of triethylamine. Crystallization of the crude product from tert.butyl methyl ether provides analytically pure compound of melting point 156° to 158° C.

Workup

  1. customPreparation
  2. customCrystallization of the crude product from tert.butyl methyl ether
  3. customprovides analytically pure compound of melting point 156° to 158° C.

Sources & evidence

ORD record
ord-86704c721ee24713a97ac5b14f74ef72
Source dataset
uspto-grants-1991_04
Patent number
US05006515

Reaction notes

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