Réaction #1585

ord-a7e627b3bd4d476c9aa919241c2544ff

Équation de réaction

O
water
Cn1c(=O)[nH]c(=O)n(-c2cc(N=c3sc(=O)n4n3CCCC4)c(F)cc2Cl)c1=O
1-{2-chloro-4-fluoro-5-[(tetrahydro-3-oxo-1H,3H-[1,3,4]thiadiazolo[3,4-a]pyridazin-1-ylidene)-amino]phenyl}-3-methyl-s-triazine-2,4,6(1H,3H,5H)-trione
O=C([O-])[O-].[K+].[K+]
potassium carbonate
C=CCBr
allyl bromide
C=CCn1c(=O)n(C)c(=O)n(-c2cc(N=c3sc(=O)n4n3CCCC4)c(F)cc2Cl)c1=O
title product
Rendement 73.3%
C=CCn1c(=O)n(C)c(=O)n(-c2cc(N=c3sc(=O)n4n3CCCC4)c(F)cc2Cl)c1=O
1-Allyl-3-{2-chloro-4-fluoro-5-[(tetrahydro-3-oxo-1H,3H-[1,3,4]thiadiazolo[3,4-a]-pyridazine-1-ylidene)amino]phenyl}-5-methyl-s-triazine-2,4,6(1H,3H,5H)-trione
Rendement 73.3%

Solvants

Conditions de réaction

Température
40°CELSIUS
Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    ExtractionThe aqueous mixture is extracted with ethyl acetate
  2. 2
    ExtractionThe organic extract
  3. 3
    Lavageis washed with water
  4. 4
    Séchagedried over anhydrous magnesium sulfate
  5. 5
    Concentrationconcentrated in vacuo

Mode opératoire

A mixture of 1-{2-chloro-4-fluoro-5-[(tetrahydro-3-oxo-1H,3H-[1,3,4]thiadiazolo[3,4-a]pyridazin-1-ylidene)-amino]phenyl}-3-methyl-s-triazine-2,4,6(1H,3H,5H)-trione (1.00 g, 2.27 mmol), potassium carbonate (0.627 g, 4.54 mmol) and allyl bromide (0.329 g, 2.72 mmol) in acetone is stirred overnight at 40° C. and poured into water. The aqueous mixture is extracted with ethyl acetate. The organic extract is washed with water, dried over anhydrous magnesium sulfate, and concentrated in vacuo to give the title product as a white glass (0.8 g) which is identified by NMR spectral analyses.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US05726126uspto-grants-1998_03