Trifluoroacetic acid → HCID 19388970, compound

HRID 1757879Notes

Reaction equation

HRID 1757879 reaction equation
CC(OC(=O)[NH:7][C:8]1[CH:13]=[C:12]([O:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[CH:11]=[C:10]([S:33][CH3:34])[CH:9]=1)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[CH3:34][S:33][C:10]1[CH:9]=[C:8]([NH2:7])[CH:13]=[C:12]([O:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[CH:11]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 54574880HCID 54574880, compound

Product 1

HCID 19388970HCID 19388970, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2.65 g (5.2 mmol) of 3-(methylthio)-5-(octadecyloxy)phenylcarbamic acid dimethylethyl ester and2.0 ml (26 mmol) of trifluoroacetic acid in 50 ml of methylene chloride waskept at room temperature for 24 hours. The mixture was concentrated at reduced pressure and the residue was treated with excess NaHCO3 solution. The product was extracted with methylene chloride and the dried extract was concentrated and recrystallized from methylene chloride-hexaneto give 1.85 g (87% yield), nap 75°-77° of 3-(methylthio)-5-(octadecyloxy)benzenamine. The nmr and mass spectra were consistent with the structure.

Workup

  1. concentrationThe mixture was concentrated at reduced pressure
  2. additionthe residue was treated with excess NaHCO3 solution
  3. extractionThe product was extracted with methylene chloride
  4. extractionthe dried extract
  5. concentrationwas concentrated
  6. customrecrystallized from methylene chloride-hexaneto

Sources & evidence

ORD record
ord-912b3c4d9570407a80718fd97f3c3d30
Source dataset
uspto-grants-1995_08
Patent number
US05446189

Reaction notes

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