Trifluoroacetic acid → HCID 56596977, compound

HRID 1776958Notes

Reaction equation

HRID 1776958 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH:14][C:15](=[O:26])[C:16]1[CH:21]=[CH:20][C:19]([NH:22][C:23](=[O:25])[CH3:24])=[CH:18][CH:17]=1)(C)(C)C.[C:28]([OH:34])([C:30]([F:33])([F:32])[F:31])=[O:29]>C(Cl)Cl>[F:31][C:30]([F:33])([F:32])[C:28]([OH:34])=[O:29].[C:23]([NH:22][C:19]1[CH:20]=[CH:21][C:16]([C:15]([NH:14][C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[NH2:7])=[O:26])=[CH:17][CH:18]=1)(=[O:25])[CH3:24]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58433956HCID 58433956, compound

Product 1

HCID 56596977HCID 56596977, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 1 L round-bottom flask, were added tert-butyl(2-(4-acetamidobenzamido) phenyl)carbamate (31.8 g, 86.2 mmol), DCM (1.60 mL) and TFA (95 mL). The reaction mixture was stirred for 2 hours before concentrating in vacuo. EtOH (95 mL) was added and concentrated in vacuo to further reduce the amount of residual TFA. MTBE (320 mL) was added, and the suspension was stirred for 2 hours. The solids were filtered, washed with MTBE (2×60 mL), and dried at 40° C. in vacuo for 18 hours to get 4-acetamido-N-(2-aminophenyl)benzamide trifluoroacetate salt (32.6 g, 99% yield, 92.2% HPLC purity).

Workup

  1. concentrationbefore concentrating in vacuo
  2. additionEtOH (95 mL) was added
  3. concentrationconcentrated in vacuo
  4. additionMTBE (320 mL) was added
  5. stirringthe suspension was stirred for 2 hours
  6. filtrationThe solids were filtered
  7. washwashed with MTBE (2×60 mL)
  8. customdried at 40° C. in vacuo for 18 hours

Sources & evidence

ORD record
ord-bd6d1c30e2304fa2b5370074287b5782
Source dataset
uspto-grants-2016_02
Patent number
US09266822B2

Reaction notes

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