Water → HCID 69517125, compound

HRID 1831250Notes

Reaction equation

HRID 1831250 reaction equation
[OH:1][C:2]1[N:7]=[CH:6][C:5]([NH:8][C:9](=[O:14])[C:10]([CH3:13])([CH3:12])[CH3:11])=[CH:4][CH:3]=1.[CH3:15][N:16]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:17](Cl)=[O:18].N12CCN(CC1)CC2.O>CN(C)C=O>[CH3:12][C:10]([CH3:11])([CH3:13])[C:9]([NH:8][C:5]1[CH:4]=[CH:3][C:2]([O:1][C:17](=[O:18])[N:16]([CH3:15])[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[N:7][CH:6]=1)=[O:14]

Participants

6

Reactant 4

HCID 962WaterHCID 9237DabcoHCID 77969Carbamic chloride, N-methyl-N-phenyl-HCID 178447230HCID 178447230, compound

Product 1

HCID 69517125HCID 69517125, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of N-(6-hydroxy-pyridin-3-yl)-2,2-dimethyl-propionamide (0.58 g, 3.00 mmol), N-methyl-N-phenylcarbamoyl chloride (0.51 g, 3.00 mmol) and 1,4-diazabicyclo[2.2.2]octane (0.34 g, 3.00 mmol) in dimethylformamide (20 ml) was stirred at room temperature for 1 hour. Water was added and a thick oil was being formed. The water was decanted and the residue was dissolved in dichloromethane. The solution was dried over sodium sulphate, filtered and evaporated in vacuo yielding the title compound (0.55 g, 56% yield) as a brown oil that solidified upon standing.

Workup

  1. customa thick oil was being formed
  2. customThe water was decanted
  3. dissolutionthe residue was dissolved in dichloromethane
  4. dry with materialThe solution was dried over sodium sulphate
  5. filtrationfiltered
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-7f9258ae5c1d44fa90705e26f8328c04
Source dataset
uspto-grants-2006_06
Patent number
US07067517B2

Reaction notes

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