HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

1-Bromo-2-methylpropane → 4-carboxy-2-isobutyl-6-[4-(methylthio)phenyl)-2H-pyridazin-3-one

HRID 7993
Notes
Print preview

Reaction equation

HRID 7993 reaction equation
C[O:2][C:3]([C:5]1[C:6](=[O:19])[NH:7][N:8]=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([S:17][CH3:18])=[CH:13][CH:12]=2)[CH:10]=1)=[O:4].C(=O)([O-])[O-].[K+].[K+].[CH2:26](Br)[CH:27]([CH3:29])[CH3:28].C(=O)([O-])O.[Na+]>CN(C)C=O>[C:3]([C:5]1[C:6](=[O:19])[N:7]([CH2:26][CH:27]([CH3:29])[CH3:28])[N:8]=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([S:17][CH3:18])=[CH:13][CH:12]=2)[CH:10]=1)([OH:2])=[O:4]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 65551-Bromo-2-methylpropaneHCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 219916864-methoxycarbonyl-6-[4-(methylthio)phenyl]-2H-pyridazin-3-one

Product 1

HCID 219916394-carboxy-2-isobutyl-6-[4-(methylthio)phenyl)-2H-pyridazin-3-oneYield 65.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 4-methoxycarbonyl-6-[4-(methylthio)-phenyl]-2H-pyridazin-3-one (8.00 g, 29.0 mmol) in N,N-dimethylformamide (80 mL) were added potassium carbonate (8.02 g, 58.0 mmol) and isobutyl bromide (4.76 g, 34.8 mmol), and the mixture was stirred at 80° C. for 2 hours. The temperature of the reaction mixture was allowed to drop back to room temperature, and a saturated aqueous solution of sodium hydrogencarbonate was added. The mixture was then extracted with ethyl acetate. The extract was washed with brine, and dried over anhydrous sodium sulfate. The solvent was distilled off. Following the procedure of Example 1 (7), the residue was reacted to yield the title compound as a yellow solid [yield: 65.1% (2 steps)].

Workup

  1. customto drop back to room temperature
  2. extractionThe mixture was then extracted with ethyl acetate
  3. washThe extract was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off
  6. customthe residue was reacted

Sources & evidence

ORD record
ord-91f9a9d242cc4d829d962d9a6373321d
Source dataset
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07087606B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes