HCID 23053853, compound → HCID 23053856, compound

HRID 1650196Notes

Reaction equation

HRID 1650196 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:20]([NH2:22])=O)[CH:5]=[C:6]([Cl:19])[C:7]=1[S:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11][CH:10]=1>O1CCCC1>[Cl:19][C:6]1[CH:5]=[C:4]([CH:3]=[C:2]([Cl:1])[C:7]=1[S:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11][CH:10]=1)[CH2:20][NH2:22]

Participants

3

Reactant 1

HCID 23053853HCID 23053853, compound

Product 1

HCID 23053856HCID 23053856, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 25 g of 3,5-dichloro-4-[(l-naphthyl)thio]benzene carboxamide in 150 ml of dry tetrahydrofuran (THF) is treated with 230 ml of 1.0 M BH3 -THF complex. The resulting solution is heated at reflux for 16 hours. The reaction mixture is cooled with ice and quenched with excess 2 N HCl. The mixture is then made basic with NaOH and extracted with methylene chloride. The combined extracts are washed with water and dried with anhydrous magnesium sulfate. Concentration under reduced pressure affords the crude product which is purified by column chromatography on silica gel.

Workup

  1. temperatureThe resulting solution is heated
  2. temperatureat reflux for 16 hours
  3. temperatureThe reaction mixture is cooled with ice
  4. customquenched with excess 2 N HCl
  5. extractionextracted with methylene chloride
  6. washThe combined extracts are washed with water
  7. dry with materialdried with anhydrous magnesium sulfate
  8. concentrationConcentration under reduced pressure

Sources & evidence

ORD record
ord-2f9700ca58a84115ad1cc9a5d21dd3f1
Source dataset
uspto-grants-1990_05
Patent number
US04923885

Reaction notes

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