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Dimethylformamide → HCID 13648724, compound

HRID 2352523
Notes
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Reaction equation

HRID 2352523 reaction equation
CN(C)C=O.[C:6]([N:10]1[C:15](=[O:16])[C:14]([Br:17])=[C:13]([SH:18])[CH:12]=[N:11]1)([CH3:9])([CH3:8])[CH3:7].[C:19]([C:23]1[CH:30]=[CH:29][C:26]([CH2:27]Br)=[CH:25][CH:24]=1)([CH3:22])([CH3:21])[CH3:20].C(=O)([O-])[O-].[Na+].[Na+]>O>[C:6]([N:10]1[C:15](=[O:16])[C:14]([Br:17])=[C:13]([S:18][CH2:27][C:26]2[CH:29]=[CH:30][C:23]([C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:24][CH:25]=2)[CH:12]=[N:11]1)([CH3:9])([CH3:7])[CH3:8]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 878361-(Bromomethyl)-4-(1,1-dimethylethyl)benzeneHCID 13648719HCID 13648719, compound

Product 1

HCID 13648724HCID 13648724, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent

Conditions

Temperature
80 °C

Procedure

To a dimethylformamide solution of 4.4 g of 2-tert.-butyl-4-bromo-5-mercapto-3(2H)-pyridazinone and 4.7 g of 4-tert.-butylbenzyl bromide was added 3.5 g of sodium carbonate. The resulting reaction liquid was stirred at 80° C. for 4 hours, allowed to cool to room temperature, incorporated with water and extracted with benzene. The benzene layer was washed with 3% aqueous solution of sodium hydroxide and then with water, dried and then freed of benzene by distillation to give yellowish brown solid. The solid was recrystallized from a mixed solvent of benzene and n-hexane to obtain white crystals (yield: 64%).

Workup

  1. customThe resulting reaction liquid
  2. extractionextracted with benzene
  3. washThe benzene layer was washed with 3% aqueous solution of sodium hydroxide
  4. dry with materialwith water, dried
  5. distillationfreed of benzene by distillation
  6. customto give yellowish brown solid
  7. customThe solid was recrystallized from a mixed solvent of benzene and n-hexane

Sources & evidence

ORD record
ord-cd15429ede1a4cb5a06a5390c59862e7
Source dataset
uspto-grants-1989_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04877787

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes