Dimethylcarbamoyl Chloride → HCID 15239994, compound

HRID 1653646Notes

Reaction equation

HRID 1653646 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[N+:11]([O-])[C:10]=1[C:16]([O:18][CH3:19])=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[Si]([N:24]=[N+:25]=[N-:26])(C)C.CN(C)C(Cl)=O.C(=O)([O-])O.[Na+]>C(#N)C>[N:24]([C:12]1[N:11]=[C:10]([C:16]([O:18][CH3:19])=[O:17])[C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:14][CH:13]=1)=[N+:25]=[N-:26]

Participants

6

Reactant 4

HCID 6598Dimethylcarbamoyl Chloride2×HCID 78378Azidotrimethylsilane2×HCID 516892Sodium BicarbonateHCID 15239991HCID 15239991, compound

Product 1

HCID 15239994HCID 15239994, compoundYield 319.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To an acetonitrile (70 ml) solution of 10 g (38.57 mmol) of methyl 3-benzyloxypicolinate N-oxide in a 200 ml round bottomed flask, 8.9 g (7.7 mmol) of trimethylsilylazide and 4.1 g (38.57 mmol) of N,N-dimethylcarbamoyl chloride were added, and the mixture was refluxed for 12 hours. Then, 4.4 g (38.5 mmol) of trimethylsilylazide and 2.1 g (19.3 mmol) of N,N-dimethylcarbamoyl chloride were further added, and the mixture was refluxed for 12 hours. After cooling, the reaction mixture was gradually added to an ice-cooled saturated sodium hydrogen carbonate aqueous solution. Formed crystals were collected by filtration, washed with water, then dissolved in dichloromethane, dried and concentrated, and then recrystallized from ethanol to obtain 7.0 g (yield: 64%) of the desired product.

Workup

  1. temperaturethe mixture was refluxed for 12 hours
  2. temperaturethe mixture was refluxed for 12 hours
  3. temperatureAfter cooling
  4. customFormed crystals
  5. filtrationwere collected by filtration
  6. washwashed with water
  7. dissolutiondissolved in dichloromethane
  8. customdried
  9. concentrationconcentrated
  10. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-22271f9427bc461592d8c163a47be0d3
Source dataset
uspto-grants-1995_04
Patent number
US05403816

Reaction notes

Loading…