Trifluoroacetic acid → 2-Aminoacetanilide

HRID 1700351Notes

Reaction equation

HRID 1700351 reaction equation
FC(F)(F)C(O)=O.[C:8]1([NH:14][C:15]([CH2:17][NH:18]C(=O)OC(C)(C)C)=[O:16])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>ClCCl>[NH2:18][CH2:17][C:15]([NH:14][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:16]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 10634424Tert-butyl n-[(phenylcarbamoyl)methyl]carbamate

Product 1

HCID 2083842-Aminoacetanilide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

40 ml of dichloromethane and 20 ml of trifluoroacetic acid were added to 687 mg (2.74 mmol) of t-butyl phenylcarbamoylmethylcarbamate, and they were stirred at room temperature for 3 hours. Dichloromethane and trifluoroacetic acid were evaporated under reduced pressure. A saturated aqueous sodium hydrogencarbonate solution was added to the residue. After the extraction with ethyl acetate and then with dichloromethane, the organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure to obtain the title compound.

Workup

  1. customDichloromethane and trifluoroacetic acid were evaporated under reduced pressure
  2. additionA saturated aqueous sodium hydrogencarbonate solution was added to the residue
  3. extractionAfter the extraction with ethyl acetate
  4. dry with materialwith dichloromethane, the organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3e3152f295594a38a18d8080cd3cea7e
Source dataset
uspto-grants-2002_02
Patent number
US06350762B1

Reaction notes

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