Pivalic acid → HCID 603365, compound

HRID 1750915Notes

Reaction equation

HRID 1750915 reaction equation
[O:1]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH:14][C:15](=[O:17])[CH3:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].C(O)(=O)C(C)(C)C.C(=O)([O-])[O-].[Na+].[Na+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH:12]1[C:13]2[C:7]3[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=3[O:1][C:8]=2[C:9]([NH:14][C:15](=[O:17])[CH3:16])=[CH:10][CH:11]=1

Participants

6

Reactant 4

HCID 6417Pivalic acidHCID 10340Sodium CarbonateHCID 11430Potassium CarbonateHCID 8970802-Phenoxyacetanilide

Product 1

HCID 603365HCID 603365, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Conditions

Temperature
105 °C

Procedure

The mixture of N-(2-phenoxyphenyl)acetamide (120 g, 528 mmol), potassium carbonate (7.30 g, 52.8 mmol), palladium acetate (11.85 g, 52.8 mmol) and pivalic acid (539 g, 5280 mmol) was prepared and heated at 105° C. (inner temperature) under air for two days. GC-MS showed 60% product. The reaction was stirred at 115° C. (inner temperature) for another night. The reaction was then cooled to room temperature and neutralized by saturated sodium carbonate solution, which was then extracted by EtOAc three times. The extraction was concentrated to give the crude product N-(dibenzo[b,d]furan-4-yl)acetamide (90 g, 76% yield) as brown solid.

Workup

  1. customwas prepared
  2. temperatureThe reaction was then cooled to room temperature
  3. extractionwas then extracted by EtOAc three times
  4. extractionThe extraction
  5. concentrationwas concentrated

Sources & evidence

ORD record
ord-039e4acf52934f75bbb54f3a6f82b3b4
Source dataset
uspto-grants-2015_10
Patent number
US09156870B2

Reaction notes

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