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Water → 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

HRID 1489
Notes
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Reaction equation

HRID 1489 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([N:9]=[C:10]2[N:14]3[CH2:15][CH2:16][CH2:17][CH2:18][N:13]3[C:12](=[O:19])[S:11]2)=[CH:4][C:3]=1[N:20]1[C:25](=[O:26])[NH:24][C:23](=[O:27])[N:22]([CH3:28])[C:21]1=[O:29].C(=O)([O-])[O-].[K+].[K+].[CH2:36](Br)[CH:37]=[CH2:38].O>CC(C)=O>[CH2:36]([N:24]1[C:23](=[O:27])[N:22]([CH3:28])[C:21](=[O:29])[N:20]([C:3]2[CH:4]=[C:5]([N:9]=[C:10]3[N:14]4[CH2:15][CH2:16][CH2:17][CH2:18][N:13]4[C:12](=[O:19])[S:11]3)[C:6]([F:8])=[CH:7][C:2]=2[Cl:1])[C:25]1=[O:26])[CH:37]=[CH2:38]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 196907301-{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

Product 1

HCID 19690757
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
Yield 73.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
40 °C

Procedure

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.

Workup

  1. extractionThe aqueous mixture is extracted with ethyl acetate
  2. extractionThe organic extract
  3. washis washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a7e627b3bd4d476c9aa919241c2544ff
Source dataset
uspto-grants-1998_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05726126

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes