Thiophenol → HCID 706762, compound

HRID 327162Notes

Reaction equation

HRID 327162 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[C:11]#[N:12].[K].[C:14]1([SH:20])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C1(S)C=CC=CC=1.[OH-].[K+]>CO.CN(C)C=O>[C:14]1([S:20][C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=2[C:11]#[N:12])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

7

Reactant 4

HCID 7969ThiophenolHCID 14797Potassium HydroxideHCID 855042-Chloro-5-nitrobenzonitrileHCID 686835543111-52-2

Product 1

HCID 706762HCID 706762, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
105 °C

Procedure

4-Chloro-3-cyanonitrobenzene (12.5 g, 6.84 mmol) was added portionwise to a stirred N,N-dimethylformamide (50 mL) solution of thiophenol potassium salt [prepared by adding thiophenol (7.1 mL, 6.9 mmol) to a solution of potassium hydroxide (3.84 g, 6.84 mmol) in methanol followed by removal of the methanol in vacuo]. After stirring at 105° C. for 2.5 hours the mixture was poured into ice-water, filtered, the collected solid washed with water, dissolved in 300 mL of refluxing ethanol (charcoal), filtered, treated with 35 mL of water and refrigerated. The resulting pale yellow solid weighed 13.3 g (76%), mp 82°-84° C. 1H--NMR (250 MHz, CDCl3): 6.93 (d, 1H, J=9.0 Hz, aromatic), 7.51-7.62 (m, 5H, aromatic), 8.12(dd, 1H, J=9.2, 2.5 Hz, aromatic), 8.46 (d, 1H, J=2.5 Hz, aromatic). MS (CI, CH4): 257(M+1).

Workup

  1. customprepared
  2. customfollowed by removal of the methanol in vacuo]
  3. additionwas poured into ice-water
  4. filtrationfiltered
  5. washthe collected solid washed with water
  6. dissolutiondissolved in 300 mL of refluxing ethanol (charcoal)
  7. filtrationfiltered
  8. additiontreated with 35 mL of water

Sources & evidence

ORD record
ord-598b0445225149e5a83d2c7ae88ca28e
Source dataset
uspto-grants-1993_12
Patent number
US05272163

Reaction notes

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