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Dichloromethane → HCID 13648724, compound

HRID 2352526
Notes
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Reaction equation

HRID 2352526 reaction equation
[OH-].[Na+].ClCCl.[C:6]([N:10]1[C:15](=[O:16])[C:14]([Br:17])=[C:13](Br)[CH:12]=[N:11]1)([CH3:9])([CH3:8])[CH3:7].[C:19]([C:23]1[CH:30]=[CH:29][C:26]([CH2:27][SH:28])=[CH:25][CH:24]=1)([CH3:22])([CH3:21])[CH3:20]>O.[Cl-].C([N+](CC)(CC)CC1C=CC=CC=1)C>[C:6]([N:10]1[C:15](=[O:16])[C:14]([Br:17])=[C:13]([S:28][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])([CH3:8])[CH3:7]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 6344Dichloromethane2×HCID 14798Sodium HydroxideHCID 27572524-tert-Butylbenzyl mercaptanHCID 13852600HCID 13852600, compound

Product 1

HCID 13648724HCID 13648724, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 66133
Benzyl triethylammonium chloride
Catalyst
HCID 962WaterSolvent

Procedure

Sodium hydroxide 0.22 g was dissolved in 5 ml of water, and thereto were added 10 ml of dichloromethane, 1.55 g of 2-tert.-butyl-4,5-dibromo-3(2H)-pyridazinone and 0.05 g of triethylbenzylammonium chloride. The resulting solution was incorporated with 0.83 g of 4-tert.-butyl-benzyl mercaptan at room temperature and then stirred for 10 hours. After completion of the reaction, about 50 ml of CH2Cl2 was added to the solution and the organic layer was separated therefrom, washed with 5% aqueous solution of sodium hydroxide and then with water, and dried over anhydrous sodium sulfate. Solvent was distilled away therefrom under reduced pressure and the resulting solid residue was recrystallized from a benzene/n-hexane mixed solvent to obtain 1.32 g of the intended compound (yield: 65%).

Workup

  1. additionwas added to the solution
  2. customthe organic layer was separated
  3. washwashed with 5% aqueous solution of sodium hydroxide
  4. dry with materialwith water, and dried over anhydrous sodium sulfate
  5. distillationSolvent was distilled away
  6. customunder reduced pressure and the resulting solid residue was recrystallized from a benzene/n-hexane mixed solvent

Sources & evidence

ORD record
ord-bb6e4d5d0b82462ea0c90b5bccaad472
Source dataset
uspto-grants-1989_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04877787

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes