5-[(3-Methoxyphenylamino)methylene]-2,2-dimethyl-1,3-dioxane-4,6-dione → HCID 178487715, compound

HRID 1644286Notes

Reaction equation

HRID 1644286 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:9][CH:10]=[C:11]2[C:16](=[O:17])OC(C)(C)OC2=O)[CH:6]=[CH:7][CH:8]=1>C1(OC2C=CC=CC=2)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:6]([C:16]([OH:17])=[CH:11][CH:10]=[N:9]2)=[CH:7][CH:8]=1

Participants

3

Reactant 1

HCID 7572485-[(3-Methoxyphenylamino)methylene]-2,2-dimethyl-1,3-dioxane-4,6-dione2×

Product 1

HCID 178487715HCID 178487715, compoundYield 45.1%

Reagents, catalysts & solvents 1

HCID 7583Diphenyl EtherSolvent

Procedure

5-{[(3-Methoxyphenyl)amino]methylene}-2,2-dimethyl-1,3-dioxane-4,6-dione (Intermediate 11, 43.5 g, 157 mmol) was added in small portions to phenylether (200 mL) at 225-260° C. under stirring. The reaction mixture was stirred for an additional 5 minutes, until the evolution of gas had stopped. The reaction mixture was cooled to room temperature and the precipitate was collected by filtration and washed with hexanes. Purification by recrystallization from methanol gave 12.4 g (45% yield) of product as a green solid, mp 210° C.

Workup

  1. stirringThe reaction mixture was stirred for an additional 5 minutes, until the evolution of gas
  2. filtrationthe precipitate was collected by filtration
  3. washwashed with hexanes
  4. customPurification
  5. customby recrystallization from methanol

Sources & evidence

ORD record
ord-088c4d01b4a54401ab3e1abc551752b4
Source dataset
uspto-grants-2012_02
Patent number
US08124602B2

Reaction notes

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