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Potassium Carbonate → HCID 9870466, compound

HRID 1275583
Notes
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Reaction equation

HRID 1275583 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:9]([NH:10][S:11]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)(=[O:13])=[O:12])=[C:8]([Br:22])[S:7][CH:6]=1)=[O:4].Cl.[N:24]1[CH:29]=[CH:28][CH:27]=[C:26]([CH2:30]Cl)[CH:25]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[CH3:1][O:2][C:3]([C:5]1[C:9]([N:10]([S:11]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)(=[O:13])=[O:12])[CH2:30][C:26]2[CH:25]=[N:24][CH:29]=[CH:28][CH:27]=2)=[C:8]([Br:22])[S:7][CH:6]=1)=[O:4]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 233943-(Chloromethyl)pyridine hydrochlorideHCID 9822596HCID 9822596, compound

Product 1

HCID 9870466HCID 9870466, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent
HCID 6228
Dimethylformamide
Solvent

Procedure

To a solution of 4.80 g (11.82 mmol) of the product of Example 17 dissolved in 5.0 mL of DMF was added 2.04 g (12.41 mmol) of 3-picolyl chloride hydrochloride and 4.89 g (35.46 mmol) of potassium carbonate. The reaction mixture was then stirred at room temperature for 18 h, diluted with water and extracted with ether. The organics were then extracted with 6N HCl solution and the aqueous acid layer was then basified with 6N NaOH solution and then extracted with ether. The resulting ether layer was dried over sodium sulfate, filtered and concentrated in vacuo to provide 4.16 g (71%) of the desired product as a tan solid. Electrospray Mass Spec: 498 (M+H).

Workup

  1. extractionextracted with ether
  2. extractionThe organics were then extracted with 6N HCl solution
  3. extractionextracted with ether
  4. dry with materialThe resulting ether layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-802ae51fbc994ca0b82c1a5b7fe05f5f
Source dataset
uspto-grants-2000_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06162814

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes