Acetic Anhydride → HCID 66811912, compound

HRID 1099554Notes

Reaction equation

HRID 1099554 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 μL, 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-44b3aca0378944a28b3c436d304e103d
Source dataset
uspto-grants-2012_03
Patent number
US08143446B2

Reaction notes

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