Methanol → 2-(2-Aminophenyl)sulfanylbenzonitrile

HRID 1609277Notes

Reaction equation

HRID 1609277 reaction equation
CO.CN(C)C=O.[N+:8]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[S:17][C:18]1[CH:25]=[CH:24][CH:23]=[CH:22][C:19]=1[C:20]#[N:21])([O-])=O>Cl.O.[Fe]>[NH2:8][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[S:17][C:18]1[CH:25]=[CH:24][CH:23]=[CH:22][C:19]=1[C:20]#[N:21]

Participants

7

Reactant 3

HCID 887MethanolHCID 6228DimethylformamideHCID 200844502-(2-Nitrophenylthio)benzonitrile

Product 1

HCID 3662332-(2-Aminophenyl)sulfanylbenzonitrile

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

In a mixture of 40 ml of concentrated hydrochloric acid, 60 ml of methanol and 40 ml of N,N-dimethylformamide was suspended 2-(2-nitrophenylthio)benzonitrile followed by addition of 8.64 g of powdered iron en bloc, and the mixture was stirred at 60° C. for 1 hour. The reaction mixture was then diluted with water and the precipitate was extracted with ether. This extract was washed with aqueous sodium hydrogen carbonate solution and water in that order and dried over magnesium sulfate. The solvent was then distilled off and the residue was subjected to column chromatography (Wakogel C200) using ethyl acetate-n-hexane (1:4) as the eluent. The crystals obtained were recrystallized from ethyl acetate-n-hexane to give 4.8 g of the title compound as white crystals, m.p. 86°-89° C.

Workup

  1. extractionthe precipitate was extracted with ether
  2. washThis extract was washed with aqueous sodium hydrogen carbonate solution and water in that order
  3. dry with materialdried over magnesium sulfate
  4. distillationThe solvent was then distilled off
  5. customThe crystals obtained
  6. customwere recrystallized from ethyl acetate-n-hexane

Sources & evidence

ORD record
ord-f02722e2835e40ffb553e2be3502ba4a
Source dataset
uspto-grants-1995_03
Patent number
US05399703

Reaction notes

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