Dimethylformamide → HCID 10562362, compound

HRID 2358651Notes

Reaction equation

HRID 2358651 reaction equation
[N+:1]([C:4]1[CH:10]=[C:9](Cl)[CH:8]=[CH:7][C:5]=1N)([O-:3])=[O:2].[C:12]1([SH:18])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[Na].C[N:21](C=O)C>C(OCC)(=O)C>[N+:1]([C:4]1[CH:10]=[C:9]([NH2:21])[CH:8]=[CH:7][C:5]=1[S:18][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 69794-Chloro-2-nitroanilineHCID 66586497Sodium benzenethiol

Product 1

HCID 10562362HCID 10562362, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-Nitro-4-chloro aniline (1.0 g, 5.79 mmol), sodium thiophenol (0.84 g, 6.4 mmol) in DMF (10 mL) was heated 2.5 h at 100° C. The mixture was cooled, diluted with ethyl acetate (100 mL) and the organic layer washed with water, 20% aqueous potassium hydroxide solution and aqueous 10% sodium chloride solution, then, dried over anhydrous sodium sulfate. The drying agent was filtered and the solvent concentrated under vacuum leaving the title compound as a red solid (0.98 g, 69%).

Workup

  1. temperatureThe mixture was cooled
  2. washthe organic layer washed with water, 20% aqueous potassium hydroxide solution and aqueous 10% sodium chloride solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationThe drying agent was filtered
  5. concentrationthe solvent concentrated under vacuum

Sources & evidence

ORD record
ord-137bb21b839b4682b26dec773d864a05
Source dataset
uspto-grants-2010_07
Patent number
US07763731B2

Reaction notes

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