3-Bromo-1,1,1-trifluoro-2-propanone → HCID 86657118, compound

HRID 468587Notes

Reaction equation

HRID 468587 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]([CH3:16])[C:12]([O:14][CH3:15])=[O:13])=[CH:7][CH:6]=1)(=[S:3])[NH2:2].Br[CH2:18][C:19](=O)[C:20]([F:23])([F:22])[F:21]>O1CCOCC1>[F:21][C:20]([F:23])([F:22])[C:19]1[N:2]=[C:1]([NH:4][C:5]2[CH:6]=[CH:7][C:8]([CH:11]([CH3:16])[C:12]([O:14][CH3:15])=[O:13])=[CH:9][CH:10]=2)[S:3][CH:18]=1

Participants

4

Reactant 2

HCID 790083-Bromo-1,1,1-trifluoro-2-propanoneHCID 86657119HCID 86657119, compound

Product 1

HCID 86657118HCID 86657118, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

In a 250 ml round-bottomed flask equipped with condenser and magnetic stirrer, a solution of methyl 2-[4-(carbamothioylamino)phenyl]propanoate (10.7 g, 48.4 mmol) in 1,4-dioxane (200 ml) was treated at room temperature with 3-bromo-1,1,1-trifluoro-propan-2-one (5 ml, 48.4 mmol) and the reaction mixture was refluxed for 2 h. After cooling at room temperature, the solvent was distilled under vacuum, the residue dissolved in CH2Cl2 (200 ml), washed with a saturated solution of NaHCO3 (3×100 ml), dried over anhydrous Na2SO4 and evaporated under vacuum to give pure methyl 2-(4-{[4-(trifluoromethyl)-1,3-thiazol-2-yl]amino}phenyl)propanoate (12.8 g, 38.7 mmol) as yellow oil (80%).

Workup

  1. customIn a 250 ml round-bottomed flask equipped with condenser and magnetic stirrer
  2. temperaturethe reaction mixture was refluxed for 2 h
  3. distillationthe solvent was distilled under vacuum
  4. dissolutionthe residue dissolved in CH2Cl2 (200 ml)
  5. washwashed with a saturated solution of NaHCO3 (3×100 ml)
  6. dry with materialdried over anhydrous Na2SO4
  7. customevaporated under vacuum

Sources & evidence

ORD record
ord-87fe556d75824b578add93d8a0ca6cab
Source dataset
uspto-grants-2014_01
Patent number
US08624036B2

Reaction notes

Loading…