Acetic Anhydride → HCID 66811912, compound

HRID 456281Notes

Reaction equation

HRID 456281 reaction equation
[CH3:1][N:2]([CH3:25])[C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][O:11][C:12]2[CH:24]=[CH:23][C:15]([C:16]([NH:18][CH2:19][C:20]([OH:22])=[O:21])=O)=[CH:14][CH:13]=2)=[CH:5][CH:4]=1.[F:26][C:27]([F:38])([F:37])[O:28][C:29]1[CH:36]=[CH:35][C:32]([CH:33]=O)=[CH:31][CH:30]=1.C([O-])(=O)C.[Na+].C(OC(=O)C)(=O)C.C(=O)([O-])O.[Na+]>C(O)C.CCCCCC>[CH3:25][N:2]([CH3:1])[C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][O:11][C:12]2[CH:13]=[CH:14][C:15]([C:16]3[O:21][C:20](=[O:22])/[C:19](=[CH:33]/[C:32]4[CH:35]=[CH:36][C:29]([O:28][C:27]([F:26])([F:37])[F:38])=[CH:30][CH:31]=4)/[N:18]=3)=[CH:23][CH:24]=2)=[CH:5][CH:4]=1

Participants

8

Reactant 5

HCID 7918Acetic AnhydrideHCID 69573p-(Trifluoromethoxy)benzaldehydeHCID 516892Sodium BicarbonateHCID 517045Sodium AcetateHCID 66812088HCID 66812088, compound

Product 1

HCID 66811912HCID 66811912, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8058HexaneSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of N-(4-{2-[4-(dimethylamino)phenyl]ethoxy}benzoyl)glycine (241 mg, 0.676 mmol) prepared in Example 23 (23b), 4-(trifluoromethoxy)benzaldehyde (106 pt, 0.742 mmol), sodium acetate (83.9 mg, 1.02 mmol), and acetic anhydride (319 μL, 3.38 mmol) was stirred at 120° C. for 15 minutes and then allowed to cool to room temperature. A saturated sodium hydrogen carbonate aqueous solution, hexane, and ethanol were added to the resulting solidified product which was washed by ultrasonic vibration. The precipitate was collected by filtration and dried by heating under reduced pressure to give 234 mg of the title compound (orange solid, yield: 70%).

Workup

  1. temperatureto cool to room temperature
  2. washwas washed by ultrasonic vibration
  3. filtrationThe precipitate was collected by filtration
  4. customdried
  5. temperatureby heating under reduced pressure

Sources & evidence

ORD record
ord-479fca27f3eb417fb02377d4bc630a97
Source dataset
uspto-grants-2013_07
Patent number
US08497397B2

Reaction notes

Loading…