Sulfuric Acid → HCID 19969455, compound

HRID 974800Notes

Reaction equation

HRID 974800 reaction equation
N[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][C:9]1[CH:16]=[C:15]([C:17]([F:20])([F:19])[F:18])[CH:14]=[CH:13][C:10]=1[C:11]#[N:12].S(=O)(=O)(O)[OH:22].[OH-].[Na+]>C(O)(=O)C.O>[F:18][C:17]([F:20])([F:19])[C:15]1[CH:14]=[CH:13][C:10]2[C:11](=[O:22])[NH:12][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=3[S:8][C:9]=2[CH:16]=1

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 19969451HCID 19969451, compound

Product 1

HCID 19969455HCID 19969455, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

2-(2-Aminophenylthio)-4-trifluoromethylbenzonitrile (12.5 g, 42.5 mmol) in glacial acetic acid (135 ml), water (135 ml), and concentrated sulphuric acid (135 ml) was heated to 125°-130° C. for 2.5 hr before being cooled and added to 1.5 l of ice-water and adjusted to pH 4 with sodium hydroxide solution (10N, 480 ml). The product was extracted into chloroform (1 l), dried (Na2SO4) and evaporated in vacuo. The light brown oil was placed in xylene (800 ml) and refluxed for 18 hr in a Dean-Stark apparatus. The title compound was obtained as off-white crystals (7.8 g. m.p. 216°-217° C., Rf 0.28, hexane/EtOAc 2:1) after reducing the volume to approximately 450 ml and allowing the solution to cool.

Workup

  1. temperaturebefore being cooled
  2. extractionThe product was extracted into chloroform (1 l)
  3. dry with materialdried (Na2SO4)
  4. customevaporated in vacuo
  5. temperaturerefluxed for 18 hr in a Dean-Stark apparatus

Sources & evidence

ORD record
ord-512fb7733cde48d782f0126e31bcc854
Source dataset
uspto-grants-1997_03
Patent number
US05607929

Reaction notes

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