Dimethylcarbamoyl Chloride → 2-Ethoxy-2-methyl-2H-1,3-benzodioxol-4-yl dimethylcarbamate

HRID 461795Notes

Reaction equation

HRID 461795 reaction equation
[CH2:1]([O:3][C:4]1([CH3:14])[O:8][C:7]2[CH:9]=[CH:10][CH:11]=[C:12]([OH:13])[C:6]=2[O:5]1)[CH3:2].[CH3:15][N:16]([CH3:20])[C:17](Cl)=[O:18].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:15][N:16]([CH3:20])[C:17](=[O:18])[O:13][C:12]1[C:6]2[O:5][C:4]([O:3][CH2:1][CH3:2])([CH3:14])[O:8][C:7]=2[CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 11430Potassium CarbonateHCID 213925462-Ethoxy-2-methyl-2H-1,3-benzodioxol-4-ol

Product 1

HCID 213925612-Ethoxy-2-methyl-2H-1,3-benzodioxol-4-yl dimethylcarbamateYield 77%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2-Ethoxy-2-methyl-4-hydroxy-1,3-benzodioxole, prepared as in Example 1, (10g) was dissolved in dry acetone (100 ml). Dimethylcarbamoylchloride (8g) and potassium carbonate (12g) were added and the mixture stirred and heated under reflux for six hours. The mixture was then filtered and the solvent evaporated from the filtrate under reduced pressure. Distillation of the residue gave 2-ethoxy-2-methyl-1,3-benzodioxol-4-yl dimethylcarbamate (9.5g, 77% yield), boiling oint 120°-124° C/0.3 mmHg.

Workup

  1. temperatureheated
  2. temperatureunder reflux for six hours
  3. filtrationThe mixture was then filtered
  4. customthe solvent evaporated from the filtrate under reduced pressure
  5. distillationDistillation of the residue

Sources & evidence

ORD record
ord-53403a33e8a648ce8b4ff460344429b6
Source dataset
uspto-grants-1977_12
Patent number
US04064250

Reaction notes

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