2,2-Dimethyl-1,3-dioxane-4,6-dione → 2,2-Dimethyl-5-[(1-methyl-1H-pyrazol-3-ylamino)-methylene]-[1,3]dioxane-4,6-dione

HRID 607152Notes

Reaction equation

HRID 607152 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][C:4]([NH2:7])=[N:3]1.[CH3:8][C:9]1([CH3:17])[O:14][C:13](=[O:15])[CH2:12][C:11](=[O:16])[O:10]1.[CH2:18](OC(OCC)OCC)C>CCO>[CH3:8][C:9]1([CH3:17])[O:14][C:13](=[O:15])[C:12](=[CH:18][NH:7][C:4]2[CH:5]=[CH:6][N:2]([CH3:1])[N:3]=2)[C:11](=[O:16])[O:10]1

Participants

5

Reactant 3

HCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 31214Ethyl orthoformateHCID 1372541-Methyl-3-aminopyrazole

Product 1

HCID 670477842,2-Dimethyl-5-[(1-methyl-1H-pyrazol-3-ylamino)-methylene]-[1,3]dioxane-4,6-dioneYield 66.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 1-methyl-1H-pyrazol-3-ylamine (1.05 g, 10.8 mmol), 2,2-dimethyl-[1,3]dioxane-4,6-dione (1.71 g, 11.9 mmol), and triethylorthoformate (1.60 g, 10.8 mmol,) in a 25 mL round bottomed flask was heated in a 100° C. oil bath for 15 min. The mixture was cooled to room temperature and EtOH (10 mL) was added. The reaction mixture was heated to dissolve all solids and then cooled back to room temperature. The solid that was formed was isolated by filtration, rinsed with ethanol, and dried to provide the title compound (1.81 g, 66% yield).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. temperatureThe reaction mixture was heated
  3. dissolutionto dissolve all solids
  4. temperaturecooled back to room temperature
  5. customThe solid that was formed
  6. customwas isolated by filtration
  7. washrinsed with ethanol
  8. customdried

Sources & evidence

ORD record
ord-4119f3aea182472485acdac3d5f669be
Source dataset
uspto-grants-2011_03
Patent number
US07915411B2

Reaction notes

Loading…