Hydrochloric Acid → HCID 21660027, compound

HRID 1176013Notes

Reaction equation

HRID 1176013 reaction equation
[CH:1]([S:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[N+:12]([O-])=O)([CH3:3])[CH3:2].Cl.[Sn]>CO>[CH:1]([S:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[NH2:12])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 5352426Tin atomHCID 595598261-[1-(Isopropylthio)methyl]-2-nitrobenzene

Product 1

HCID 21660027HCID 21660027, compoundYield 45.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

11.8 g (55.6 mmol) 1-[1-(isopropylthio)methyl]-2-nitrobenzene (VII-2) in 150 ml methanol are placed in a 500 ml three-necked flask equipped with a stirrer and thermometer, mixed with 150 ml concentrated hydrochloric acid with stirring, and 17.6 g powdered tin (148.5 mmol) are added in portions at 20-40° C. Stirring of the mixture wird is continued at 40° C. for about an hour. The reaction is cooled, filtered and mixed with 1300 ml of an ice-cooled 10% sodium hydroxide solution. Then it is extracted twice with dichloromethane, dried over sodium sulfate, and the solvent is evaporated under vacuum. The crude product is purified on silica gel with 3:1 hexane/methyl t-butyl ether. 4.6 g (94.6% purity by HPLC, 43.2% theoretical yield) of 2-[1-(isopropylthio)methyl]aniline are obtained as a yellow oil [logP (pH 2.3)=1.94].

Workup

  1. customequipped with a stirrer
  2. stirringStirring of the mixture wird
  3. waitis continued at 40° C. for about an hour
  4. temperatureThe reaction is cooled
  5. filtrationfiltered
  6. additionmixed with 1300 ml of an ice-
  7. temperaturecooled 10% sodium hydroxide solution
  8. extractionThen it is extracted twice with dichloromethane
  9. dry with materialdried over sodium sulfate
  10. customthe solvent is evaporated under vacuum
  11. customThe crude product is purified on silica gel with 3:1 hexane/methyl t-butyl ether

Sources & evidence

ORD record
ord-c042e9b261544a5b8cab1ac364d75fd1
Source dataset
uspto-grants-2010_11
Patent number
US07842710B2

Reaction notes

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