Hydrochloric Acid → HCID 67173093, compound

HRID 1256156Notes

Reaction equation

HRID 1256156 reaction equation
[CH3:1][S:2][CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-])=O)[CH:6]=1.Cl>CO.[Fe]>[CH3:1][S:2][CH2:3][CH2:4][C:5]1[CH:6]=[C:7]([CH:8]=[CH:9][CH:10]=1)[NH2:11]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 56615066HCID 56615066, compound

Product 1

HCID 67173093HCID 67173093, compoundYield 95.1%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 887MethanolSolvent

Procedure

A mixture of methyl(3-nitrophenethyl)sulfane (4.4 g, 22 mmol) and iron powder (3.75 g, 67 mmol) in MeOH was stirred at room temperature, then aqueous HCl (20 g, 36.5%) was added slowly, then the mixture solution was heated to reflux for 3 hours. The solvent was evaporated, and saturated sodium bicarbonate was added, the aqueous layer was extracted with ethyl acetate 3 times. The combined organic phase was washed with brine, dried over sodium sulfate and concentrated to give 3-(2-(methylthio)ethyl)aniline (3.5 g, yield 94%). 1H NMR: 400 MHz CDCl3 δ 7.11-7.07 (m, 1H), 6.63-6.61 (m, 1H), 6.56-6.54 (m, 1H), 3.64 (s, 2H), 2.83-2.71 (m, 4H), 2.13 (s, 3H).

Workup

  1. temperaturethe mixture solution was heated
  2. temperatureto reflux for 3 hours
  3. customThe solvent was evaporated
  4. additionsaturated sodium bicarbonate was added
  5. extractionthe aqueous layer was extracted with ethyl acetate 3 times
  6. washThe combined organic phase was washed with brine
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-7ccf0b8e1c8242d48759661a2b34ed46
Source dataset
uspto-grants-2013_06
Patent number
US08461134B2

Reaction notes

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