Sulfuryl chloride → HCID 9966327, compound

HRID 650149Notes

Reaction equation

HRID 650149 reaction equation
[CH2:1]([C:3]1[C:12]2[O:11][CH:10]([C:13]([F:16])([F:15])[F:14])[C:9]([C:17]([OH:19])=[O:18])=[CH:8][C:7]=2[CH:6]=[CH:5][CH:4]=1)[CH3:2].S(Cl)([Cl:23])(=O)=O>COP(OC)(OC)=O.O>[Cl:23][C:5]1[CH:4]=[C:3]([CH2:1][CH3:2])[C:12]2[O:11][CH:10]([C:13]([F:14])([F:15])[F:16])[C:9]([C:17]([OH:19])=[O:18])=[CH:8][C:7]=2[CH:6]=1

Participants

5

Reactant 2

HCID 24648Sulfuryl chlorideHCID 15458899HCID 15458899, compound

Product 1

HCID 9966327HCID 9966327, compoundYield 117.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 10541Trimethyl PhosphateSolvent

Conditions

Temperature
0 °C

Procedure

8-Ethyl-2-(trifluoromethyl)2H-1-benzopyran-3-carboxylic acid (Example 28) (0.68 g, 2.5 mmol) was dissolved in trimethylphosphate (5 mL) and was treated with sulfuryl chloride (0.35 g, 2.62 mmol) at 0° C. After stirring at 0° C. for 45 minutes and 1 hour at room temperature, the reaction was diluted with cold water (15 mL). The resulting oily mixture was extracted with hexanes-ethyl acetate. The organic phase was washed with brine, dried, and concentrated in vacuo yielding the title compound as a solid (0.9 g, 117%): mp 197.2-199.1° C. 1H NMR (acetone-d6/300 MHz) 7.86 (s, 1H), 7.38 (d, 1H, J=2.7 Hz), 7.30 (d, 1H, J=2.4 Hz), 5.88 (q, 1H, J=7.2 Hz), 2.65 (m, 2H), 1.19 (t, 3H, J=7.5 Hz). FABLRMS m/z 307 (M+H). Anal. Calc'd for C13H10ClF3O3: C, 50.92; H, 3.29. Found: C, 51.00; H, 3.23.

Workup

  1. extractionThe resulting oily mixture was extracted with hexanes-ethyl acetate
  2. washThe organic phase was washed with brine
  3. customdried
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8dec9351f46143ad810a621b32acf147
Source dataset
uspto-grants-2001_08
Patent number
US06271253B1

Reaction notes

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