Hexane → HCID 117899720, compound

HRID 522437Notes

Reaction equation

HRID 522437 reaction equation
[CH3:1][C:2]1[CH:8]=[CH:7][C:5](N)=[CH:4][C:3]=1[S:9][CH2:10][C:11]([F:14])([F:13])[F:12].N([O-])=[O:16].[Na+].CCCCCC.C(OCC)(=O)C>O.S(=O)(=O)(O)O.S([O-])([O-])(=O)=O.[Cu+2]>[CH3:1][C:2]1[CH:8]=[CH:7][C:5]([OH:16])=[CH:4][C:3]=1[S:9][CH2:10][C:11]([F:14])([F:13])[F:12]

Participants

8

Reactant 4

HCID 8058HexaneHCID 8857Ethyl AcetateHCID 23668193Sodium NitriteHCID 79141260HCID 79141260, compound

Product 1

HCID 117899720HCID 117899720, compoundYield 38%

Reagents, catalysts & solvents 3

HCID 24462Copper SulfateCatalystHCID 962WaterSolventHCID 1118Sulfuric AcidSolvent2×

Conditions

Temperature
2.5 °C

Procedure

49.7 g (225 mmol) of 4-methyl-3-(2,2,2-trifluoroethylthio)aniline was suspended in 500 ml of a 15% aqueous sulfuric acid solution. Thereinto was dropwise added an aqueous solution obtained by dissolving 18.6 g (270 mmol) of sodium nitrite in 100 ml of water, at 0 to 5° C. with ice-cooling. After the completion of the dropwise addition, the mixture was stirred for 1 hour with the temperature being kept. The reaction mixture was gradually dropped at 120° C. into a solution obtained by dissolving 71.8 g (450 mmol) of anhydrous copper sulfate in 400 ml of 60% sulfuric acid. The mixture was allowed to cool to room temperature and subjected to extraction with ethyl acetate. The organic phase obtained was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The crude product obtained was purified by column chromatography (developing solvent: a mixed solvent of n-hexane:ethyl acetate=10:1), to obtain 19 g (yield: 38%) of an intended product.

Workup

  1. additionThereinto was dropwise added an aqueous solution
  2. customobtained
  3. additionAfter the completion of the dropwise addition
  4. additionThe reaction mixture was gradually dropped at 120° C. into a solution
  5. customobtained
  6. temperatureto cool to room temperature
  7. extractionsubjected to extraction with ethyl acetate
  8. customThe organic phase obtained
  9. dry with materialwas dried over anhydrous magnesium sulfate
  10. concentrationconcentrated under reduced pressure
  11. customThe crude product obtained
  12. customwas purified by column chromatography (

Sources & evidence

ORD record
ord-5d7eca1afc934b9bae126bd17f047e03
Source dataset
uspto-grants-2016_05
Patent number
US09332754B2

Reaction notes

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