Sulfuric Acid → HCID 13579318, compound

HRID 1589097Notes

Reaction equation

HRID 1589097 reaction equation
[F:1][C:2]([F:21])([F:20])[C:3]1[CH:4]=[C:5]([CH:9]([C:12](=[O:19])[CH:13]([O:17]C)[CH:14]([CH3:16])[CH3:15])[C:10]#[N:11])[CH:6]=[CH:7][CH:8]=1.S(=O)(=O)(O)O>C(O)(=O)C>[CH:14]([CH:13]1[C:12](=[O:19])[C:9]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:21])([F:20])[F:1])[CH:4]=2)=[C:10]([NH2:11])[O:17]1)([CH3:16])[CH3:15]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 20247547HCID 20247547, compound

Product 1

HCID 13579318HCID 13579318, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

In this example, a mixture containing 11.4 g of (3-trifluoromethylphenyl)-(2-methoxyisovaleryl)acetonitrile and 7.8 g of concentrated sulfuric acid in 50 ml of acetic acid was warmed to reflux for 30 minutes and then concentrated by evaporation under vacuum. The concentrate was mixed with diethylether, washed three times with 1N aqueous sodium hydroxide, dried over magnesium sulfate and concentrated by evaporation affording an oil. The oil was triturated in 20% (vol.) ethyl acetate:80% petroleum ether and allowed to stand overnight (14-16 hours). The solids were collected by filtration and washed three times with 20% (vol.) ethyl acetate:80% petroleum ethyl affording 2.9 g of the title compound.

Workup

  1. temperaturewas warmed
  2. temperatureto reflux for 30 minutes
  3. concentrationconcentrated by evaporation under vacuum
  4. additionThe concentrate was mixed with diethylether
  5. washwashed three times with 1N aqueous sodium hydroxide
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated by evaporation
  8. customaffording an oil
  9. customThe oil was triturated in 20% (vol.) ethyl acetate
  10. custom(14-16 hours)
  11. filtrationThe solids were collected by filtration
  12. washwashed three times with 20% (vol.) ethyl acetate

Sources & evidence

ORD record
ord-6c600416149842539b91338fc72b6165
Source dataset
uspto-grants-1986_02
Patent number
US04568376

Reaction notes

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