Water → HCID 69518446, compound

HRID 1179872Notes

Reaction equation

HRID 1179872 reaction equation
[OH:1][C:2]1[N:7]=[CH:6][C:5]([NH:8][C:9](=[O:16])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.[CH3:17][N:18]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:19](Cl)=[O:20].N12CCN(CC1)CC2.O>CN(C)C=O>[C:9]([NH:8][C:5]1[CH:4]=[CH:3][C:2]([O:1][C:19](=[O:20])[N:18]([CH3:17])[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[N:7][CH:6]=1)(=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 962WaterHCID 9237DabcoHCID 77969Carbamic chloride, N-methyl-N-phenyl-HCID 178522251HCID 178522251, compound

Product 1

HCID 69518446HCID 69518446, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of N-(6-hydroxy-pyridin-3-yl)-benzamide (0.64 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 (15 ml) was stirred at room temperature for 1 hour. Water was added and the precipitates were collected by suction. The solids were dissolved in dichloromethane and the solution was dried over sodium sulphate, filtered and evaporated in vacuo. The residue was dissolved in ethyl acetate and filtered over a short pad of silica. Evaporation of the solvent in vacuo yielded the title compound (0.70 g, 68% yield) as a thick oil.

Workup

  1. customthe precipitates were collected by suction
  2. dissolutionThe solids were dissolved in dichloromethane
  3. dry with materialthe solution was dried over sodium sulphate
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. dissolutionThe residue was dissolved in ethyl acetate
  7. filtrationfiltered over a short pad of silica
  8. customEvaporation of the solvent in vacuo

Sources & evidence

ORD record
ord-0d95e5d68d524d37b1379b3ee8471ced
Source dataset
uspto-grants-2007_10
Patent number
US07279470B2

Reaction notes

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