N-Methyl-D-glucamine → HCID 14766065, compound

HRID 2081827Notes

Reaction equation

HRID 2081827 reaction equation
[CH3:1][NH:2][CH2:3][C@@H:4]([C@H:6]([C@@H:8]([C@@H:10]([CH2:12][OH:13])[OH:11])[OH:9])[OH:7])[OH:5].N([O-])=O.[Na+].[OH-].[K+].[C:20](Cl)(=[O:23])[CH:21]=[CH2:22].C(N[C@H]([C@H]([C@@H]([C@@H](CO)O)O)O)CO)(=O)C=C>O.C(Cl)Cl>[C:20]([N:2]([CH3:1])[CH2:3][C@@H:4]([C@H:6]([C@@H:8]([C@@H:10]([CH2:12][OH:13])[OH:11])[OH:9])[OH:7])[OH:5])(=[O:23])[CH:21]=[CH2:22]

Participants

8

Reactant 5

HCID 8567N-Methyl-D-glucamineHCID 13140Acryloyl chlorideHCID 14797Potassium HydroxideHCID 18649787HCID 18649787, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 14766065HCID 14766065, compoundYield 41%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent

Procedure

N-methyl-1-amino-1-deoxy-D-glucitol (0.5 mol, 97.6 g) was dissolved in about 300 ml of water. Then 1-2 g of sodium nitrite was added and the solution was cooled in an ice bath. Potassium hydroxide (0.6 mole) was dissolved in water and cooled. Acryloyl chloride (0.55 mole) was mixed with an equal volume of methylene chloride. The reaction was done in the same way as described in step 3 for the synthesis of N-acryloyl-2-amino-2-deoxy-D-glucitol. The salts were also removed as described above. However, even after several weeks long evaporation from a crystallization dish, the product was not dry. After addition of more polymerization inhibitor, drying was continued in a desiccator. The semi-dry mass (yield 41-60%) was dissolved in warm dioxane which contained p-methoxy phenol. The warm solution was filtered through Celite and upon cooling the crystals were formed. They were collected and recrystallized from dioxane. The title compound is very hygroscopic.

Workup

  1. temperaturethe solution was cooled in an ice bath
  2. temperaturecooled
  3. customThe salts were also removed
  4. customHowever, even after several weeks long evaporation from a crystallization dish
  5. customthe product was not dry
  6. additionAfter addition of more polymerization inhibitor
  7. customdrying
  8. customwas continued in a desiccator
  9. dissolutionThe semi-dry mass (yield 41-60%) was dissolved in warm dioxane which
  10. filtrationThe warm solution was filtered through Celite
  11. temperatureupon cooling the crystals
  12. customwere formed
  13. customThey were collected
  14. customrecrystallized from dioxane

Sources & evidence

ORD record
ord-f1df9c789475479d817c1099e8aa1276
Source dataset
uspto-grants-1993_02
Patent number
US05185466

Reaction notes

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