Phosphorus oxychloride → 1140917-14-1

HRID 452938Notes

Reaction equation

HRID 452938 reaction equation
[F:1][C:2]([F:10])([F:9])[C:3]1([C:6](O)=O)[CH2:5][CH2:4]1.[NH2:11][NH:12][C:13]([NH2:15])=[S:14].P(Cl)(Cl)(Cl)=O>O1CCOCC1.C(OCC)(=O)C>[F:1][C:2]([F:10])([F:9])[C:3]1([C:6]2[S:14][C:13]([NH2:15])=[N:12][N:11]=2)[CH2:5][CH2:4]1

Participants

6

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 2723789ThiosemicarbazideHCID 27783061-(Trifluoromethyl)cyclopropane-1-carboxylic acid

Product 1

HCID 675442031140917-14-1Yield 37%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 1-(trifluoromethyl)cyclopropanecarboxylic acid (1 g, 6.5 mmol) and thiosemicarbazide (0.6 g, 6.5 mmol) in dioxane (8 mL) was heated to 90° C. To the hot reaction mixture was added phosphorus oxychloride (0.6 mL, 6.5 mmol). The reaction mixture was stirred at 90° C. for 16 h. The reaction mixture was then cooled, diluted with ethyl acetate (10 mL) and quenched with saturated NaHCO3 (10 mL). The aqueous layer was extracted with ethyl acetate (2×10 mL). The combined organic extracts were washed with water (15 mL), dried (Na2SO4), filtered and concentrated. The residue was triturated in hot hexanes to afford 0.5 g (37%) of the title compound. LC/MS (ESI+) m/z 210 (M+H)+.

Workup

  1. temperatureThe reaction mixture was then cooled
  2. customquenched with saturated NaHCO3 (10 mL)
  3. extractionThe aqueous layer was extracted with ethyl acetate (2×10 mL)
  4. washThe combined organic extracts were washed with water (15 mL)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was triturated in hot hexanes

Sources & evidence

ORD record
ord-51a37f49ea80454984ac8baec1350e09
Source dataset
uspto-grants-2013_07
Patent number
US08492371B2

Reaction notes

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