2,2-Dimethyl-1,3-dioxane-4,6-dione → HCID 17138478, compound

HRID 2277365Notes

Reaction equation

HRID 2277365 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([NH2:15])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:16][C:17]1([CH3:25])[O:22][C:21](=[O:23])[CH2:20][C:19](=[O:24])[O:18]1.[CH2:26](OC(OCC)OCC)C>CCO>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([NH:15][CH:26]=[C:20]2[C:21](=[O:23])[O:22][C:17]([CH3:25])([CH3:16])[O:18][C:19]2=[O:24])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 31214Ethyl orthoformateHCID 928923-Benzyloxyaniline

Product 1

HCID 17138478HCID 17138478, compoundYield 98.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 3-(Benzyloxy)benzenamine (970 g, 4.9 mol, Wuhan Xinghuayuan Tech. Co. Ltd.) and 2,2-dimethyl-1,3-dioxane-4,6-dione (842.3 g, 5.8 mol) in anhydrous EtOH (970 mL) was added triethoxymethane (865.7 g, 5.8 mol). The suspension was heated to reflux for 1 hour. The reaction mixture was then cooled to room temperature, and continued to stir for additional 2 hours. The suspension was filtered, and the solid was stirred in anhydrous EtOH (970 mL) for 2 hours, collected by filtration. The solid was dried in vacuo at 45° C. to give the title compound as a pale yellow solid (1.7 kg, 96.5%).

Workup

  1. temperatureThe suspension was heated
  2. temperatureto reflux for 1 hour
  3. filtrationThe suspension was filtered
  4. stirringthe solid was stirred in anhydrous EtOH (970 mL) for 2 hours
  5. filtrationcollected by filtration
  6. customThe solid was dried in vacuo at 45° C.

Sources & evidence

ORD record
ord-756f663b80504a1d949cf6d17835ed08
Source dataset
uspto-grants-2015_09
Patent number
US09133162B2

Reaction notes

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