Hydrochloric Acid → 2-(Phenylthio)aniline

HRID 1785754Notes

Reaction equation

HRID 1785754 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-15c9f15ab1dd4501a62f94755b1ce629
Source dataset
uspto-grants-2009_03
Patent number
US07504512B2

Reaction notes

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