Hydrochloric Acid → 2-(Phenylthio)aniline

HRID 2356006Notes

Reaction equation

HRID 2356006 reaction equation
F[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-])=O.[C:11]1([SH:17])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.Cl.O.O.[Sn](Cl)Cl>C1COCC1.C(N(CC)CC)C>[C:11]1([S:17][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[NH2:8])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7969ThiophenolHCID 61436Stannous chloride dihydrateHCID 738951-Fluoro-2-nitrobenzene

Product 1

HCID 3653932-(Phenylthio)aniline

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

A room temperature solution of 2-fluoronitrobenzene (1.41 g, 10.0 mmol), thiophenol (1.21 g, 11.0 mmol), and triethylamine (2 mL) in THF (20 mL) was stirred for 16 hours, treated with 3M HCl (10 mL) and tin(II) chloride dihydrate (11.4 g, 50 mmol), stirred for 4 hours, and extracted with ethyl acetate (50 mL). The combined extracts were dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 50% hexanes/dichloromethane to provide the desired product. MS (DCI) m/e 202 (M+H)+.

Workup

  1. extractionextracted with ethyl acetate (50 mL)
  2. dry with materialThe combined extracts were dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe concentrate was purified by flash column chromatography on silica gel with 50% hexanes/dichloromethane

Sources & evidence

ORD record
ord-a4299dfccb274adba822724daf997d4b
Source dataset
uspto-grants-2010_07
Patent number
US07754886B2

Reaction notes

Loading…