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Stannous chloride dihydrate → Benzenamine, 2-((trifluoromethyl)thio)-

HRID 566639
Notes
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Reaction equation

HRID 566639 reaction equation
O.O.[Sn](Cl)Cl.[F:6][C:7]([S:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[N+:17]([O-])=O)([F:9])[F:8]>Cl.C(O)C>[F:6][C:7]([S:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[NH2:17])([F:9])[F:8]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 98159152-Nitrophenyl trifluoromethyl sulfide

Product 1

HCID 67670Benzenamine, 2-((trifluoromethyl)thio)-Yield 75.7%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 25.53 g of tin(II) chloride dihydrate in 40 ml of concentrated hydrochloric acid was added dropwise to a stirred solution of 5.05 g of 2-nitrophenyl trifluoromethyl sulfide, obtained according to Example 1, in 30 ml of ethanol. After the addition had ended, the mixture was heated to 100° C. and stirred at this temperature for 1.5 hours. The mixture was cooled, ethanol was evaporated off under reduced pressure, and the residue was poured into a mixture of 150 g of ice and 150 ml of 40% strength by weight aqueous sodium hydroxide solution. The product was extracted with ether. The combined ether extracts were dried over magnesium sulfate and concentrated under reduced pressure. Vacuum distillation of the residue gave 3.31 g (75.7% of theory) of 2-aminophenyl trifluoromethyl sulfide (boiling point 102-104° C. at 50 mbar, melting point: 30-31° C.).

Workup

  1. customobtained
  2. additionAfter the addition
  3. temperatureThe mixture was cooled
  4. customethanol was evaporated off under reduced pressure
  5. additionthe residue was poured into a mixture of 150 g of ice and 150 ml of 40% strength by weight aqueous sodium hydroxide solution
  6. extractionThe product was extracted with ether
  7. dry with materialThe combined ether extracts were dried over magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. distillationVacuum distillation of the residue

Sources & evidence

ORD record
ord-3bf0986a95094df794209f16e30c6c5a
Source dataset
uspto-grants-2001_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06175042B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes