3-Bromo-1,1,1-trifluoro-2-propanone → HCID 86645967, compound

HRID 1094314Notes

Reaction equation

HRID 1094314 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([C@@H: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]([C@@H: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 86645968HCID 86645968, compound

Product 1

HCID 86645967HCID 86645967, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of methyl (2R)-2-[4-(carbamothioylamino)phenyl]propanoate (10.7 g, 0.0484 mol) in dioxane (200 ml) was treated at room temperature with 3-bromo-1,1,1-trifluoro-propan-2-one (5 ml, 0.0484 mol) and the resulting mixture was refluxed for 2 h. After cooling at room temperature, the solvent was evaporated under vacuum, the crude diluted with CH2Cl2 (200 ml) and washed with a saturated NaHCO3 aqueous solution (3×100 ml), dried over anhydrous Na2SO4 and evaporated to give pure methyl (2R)-2-(4-{[4-(trifluoromethyl)-1,3-thiazol-2-yl]amino}phenyl)propanoate (12.8 g, 38.7 mmol) as yellow oil (80%). 1H-NMR (CDCl3): δ 8.65 (bs, 1H, NH), 7.30 (m, 4H), 7.05 (s, 1H), 3.75 (q, 1H, J=7 Hz), 3.65 (s, 3H), 1.50 (d, 3H, J=7 Hz).

Workup

  1. temperaturethe resulting mixture was refluxed for 2 h
  2. customthe solvent was evaporated under vacuum
  3. additionthe crude diluted with CH2Cl2 (200 ml)
  4. washwashed with a saturated NaHCO3 aqueous solution (3×100 ml)
  5. dry with materialdried over anhydrous Na2SO4
  6. customevaporated

Sources & evidence

ORD record
ord-7f4a1872e2f348ada160c3520d351531
Source dataset
uspto-grants-2012_03
Patent number
US08133911B2

Reaction notes

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