Trimethyl orthoformate → HCID 67317382, compound

HRID 1042861Notes

Reaction equation

HRID 1042861 reaction equation
[CH3:1][C:2]1([CH3:10])[O:7][C:6](=[O:8])[CH2:5][C:4](=[O:9])[O:3]1.[F:11][C:12]([F:22])([F:21])[O:13][C:14]1[CH:20]=[CH:19][C:17]([NH2:18])=[CH:16][CH:15]=1.[CH:23](OC)(OC)OC>CCCCCC>[CH3:1][C:2]1([CH3:10])[O:7][C:6](=[O:8])[C:5](=[CH:23][NH:18][C:17]2[CH:19]=[CH:20][C:14]([O:13][C:12]([F:21])([F:22])[F:11])=[CH:15][CH:16]=2)[C:4](=[O:9])[O:3]1

Participants

5

Reactant 3

HCID 9005Trimethyl orthoformateHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 6008484-(Trifluoromethoxy)aniline

Product 1

HCID 67317382HCID 67317382, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
100 °C

Procedure

In a 48 mL sealed tube was dissolved 2,2-dimethyl-1,3-dioxane-4,6-dione (0.81 g, 5.6 mmol) in trimethyl orthoformate (5.6 mL). The mixture was heated to 100° C. and stirred for 2 h. To the mixture was added 4-(trifluoromethoxy)aniline (0.76 mL, 5.6 mmol) and it was stirred at 100° C. for 3 hours. The reaction was cooled to RT, diluted with hexane, filtered, and the filtered solids were air dried to yield 2,2-dimethyl-5-((4-(trifluoromethoxy)phenylamino)methylene)-1,3-dioxane-4,6-dione as a light yellow solid. MS [M+H]=332.0; Calc'd 331.2 for C14H12F3NO5.

Workup

  1. customIn a 48 mL sealed tube
  2. stirringwas stirred at 100° C. for 3 hours
  3. temperatureThe reaction was cooled to RT
  4. filtrationfiltered
  5. customdried

Sources & evidence

ORD record
ord-9c8dc702351947c9b35ee0ef07f32494
Source dataset
uspto-grants-2013_10
Patent number
US08557816B2

Reaction notes

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