Hydrochloric Acid → 2-(Phenylthio)aniline

HRID 2085672Notes

Reaction equation

HRID 2085672 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 hour, 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-76c022d9ca024a688fae21aadc272efd
Source dataset
uspto-grants-2004_04
Patent number
US06720338B2

Reaction notes

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