Trifluoroacetic acid → HCID 22351019, compound

HRID 747502Notes

Reaction equation

HRID 747502 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([CH2:20][CH2:21][NH:22]C(=O)OC(C)(C)C)[C:10](=[N:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[S:11][CH:12]=2)=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>O>[NH2:22][CH2:21][CH2:20][N:9]1[C:8]([C:5]2[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=2)=[CH:12][S:11][C:10]1=[N:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 22351010HCID 22351010, compound

Product 1

HCID 22351019HCID 22351019, compoundYield 79.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of t-butyl 2-[4-(4-bromophenyl)-2-(phenylimino)-thiazol-3(2H)-yl]ethylcarbamate (1.5 g), trifluoroacetic acid (10 ml) and water (5 ml) was stirred at room temperature for 2 hours. The reaction mixture was concentrated under reduced pressure, and to the residue was added a saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with chloroform. The organic layer was washed with a saturated brine, dried over sodium sulfate, and the solvent was evaporated. The residue was crystallized from n-hexane to give the title compound (937 mg).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionto the residue was added a saturated aqueous sodium hydrogen carbonate solution
  3. extractionthe mixture was extracted with chloroform
  4. washThe organic layer was washed with a saturated brine
  5. dry with materialdried over sodium sulfate
  6. customthe solvent was evaporated
  7. customThe residue was crystallized from n-hexane

Sources & evidence

ORD record
ord-f00ec906151a43c4a6315e7a5d9789c0
Source dataset
uspto-grants-2008_07
Patent number
US07396842B2

Reaction notes

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