Sulfuric Acid → HCID 17930983, compound

HRID 900439Notes

Reaction equation

HRID 900439 reaction equation
[NH2:1][C:2]1[S:3][C:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:5]([C:9]([F:12])([F:11])[F:10])[C:6]=1[C:7]#[N:8].S(=O)(=O)(O)[OH:20].C(=O)(O)[O-].[Na+]>>[NH2:1][C:2]1[S:3][C:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:5]([C:9]([F:10])([F:12])[F:11])[C:6]=1[C:7]([NH2:8])=[O:20]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 179309512-Amino-5-phenyl-4-(trifluoromethyl)-3-thiophenecarbonitrile

Product 1

HCID 17930983HCID 17930983, compound

Conditions

Temperature
50 °C

Procedure

A mixture of 2-amino-4-trifluoromethyl-5-phenyl-3-thiophenenitrile (0.12 g) and concentrated sulphuric acid (1.5 ml) was stirred and heated at 50° C. for 8 h. The reaction mixture was added to saturated aqueous sodium bicarbonate until a pH of 7 was obtained. The product was extracted into ethyl acetate (100 ml) and the organic layer was dried with anhydrous sodium sulfate (3 g), filtered and concentrated. The residue was chromatographed on silica gel eluting with ethyl acetate/isohexane mixtures. The solvent was removed and the product collected (0.07 g).

Workup

  1. customwas obtained
  2. extractionThe product was extracted into ethyl acetate (100 ml)
  3. dry with materialthe organic layer was dried with anhydrous sodium sulfate (3 g)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was chromatographed on silica gel eluting with ethyl acetate/isohexane mixtures
  7. customThe solvent was removed
  8. customthe product collected (0.07 g)

Sources & evidence

ORD record
ord-eb6ef6370da04431a0d42e3242612ebb
Source dataset
uspto-grants-2008_04
Patent number
US07358376B2

Reaction notes

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