Trifluoroacetic acid → 2-anilino-N-[4-(4-pyridinyl)phenyl]acetamide bis(trifluoroacetate)

HRID 1510218Notes

Reaction equation

HRID 1510218 reaction equation
C(OC(=O)[N:7]([CH2:14][C:15](=[O:29])[NH:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=2)=[CH:19][CH:18]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)(C)(C)C.[F:31][C:32]([F:37])([F:36])[C:33]([OH:35])=[O:34]>ClCCl>[F:31][C:32]([F:37])([F:36])[C:33]([OH:35])=[O:34].[F:31][C:32]([F:37])([F:36])[C:33]([OH:35])=[O:34].[NH:7]([CH2:14][C:15]([NH:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[CH:24]=[CH:25][N:26]=[CH:27][CH:28]=2)=[CH:19][CH:18]=1)=[O:29])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69078964tert-Butyl(2-oxo-2-{[4-(4-pyridinyl)phenyl]amino}ethyl)phenylcarbamate

Product 1

HCID 866297492-anilino-N-[4-(4-pyridinyl)phenyl]acetamide bis(trifluoroacetate)

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl(2-oxo-2-{[4-(4-pyridinyl)phenyl]amino}ethyl)phenylcarbamate (1.30 g) was dissolved in 50% trifluoroacetic acid in dichloromethane (26 mL) and the mixture was stirred at ambient temperature for 2 hours. The solvent was evaporated in vacuo and the residue was crystallized from n-hexane-ethyl acetate (1:1, 15 mL). The crystals were collected by filtration and washed with n-hexane/ethyl acetate (1:1, 5 mL) to afford 2-anilino-N-[4-(4-pyridinyl)phenyl]acetamide bis(trifluoroacetate) (1.46 g) as yellow crystals.

Workup

  1. customThe solvent was evaporated in vacuo
  2. customthe residue was crystallized from n-hexane-ethyl acetate (1:1, 15 mL)
  3. filtrationThe crystals were collected by filtration
  4. washwashed with n-hexane/ethyl acetate (1:1, 5 mL)

Sources & evidence

ORD record
ord-1231a0314b304bd783795410002d9b26
Source dataset
uspto-grants-2012_07
Patent number
US08211919B2

Reaction notes

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