3-Chloro-2-nitroaniline → 3-(Methylthio)-2-nitroaniline

HRID 657520Notes

Reaction equation

HRID 657520 reaction equation
Cl[C:2]1[C:3]([N+:9]([O-:11])=[O:10])=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].[CH3:12][S-:13].[Na+]>CN(C=O)C>[CH3:12][S:13][C:2]1[C:3]([N+:9]([O-:11])=[O:10])=[C:4]([NH2:5])[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 1010683-Chloro-2-nitroanilineHCID 4378561Sodium methanethiolate

Product 1

HCID 109761553-(Methylthio)-2-nitroanilineYield 38.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

20 g of 3-chloro-2-nitroaniline are dissolved in 230 ml of dry DMF. The mixture was cooled to 0° C. and sodium methanethiolate (10 g) was added portionwise. The mixture was stirred for 2 h at 20° C. The solvent was evaporated in vacuo and the residue taken up in water and EA (200 ml each). The aqueous layer was extracted with EA, and the combined organic phases were washed with brine and dried over sodium sulfate. The solvent was removed in vacuo. The crude product was purified by flash chromatography (300 g silica gel; cyclohexane/EA, gradient from 100:0 to 50:50). 8.3 g of the title compound were obtained as a red solid.

Workup

  1. customThe solvent was evaporated in vacuo
  2. extractionThe aqueous layer was extracted with EA
  3. washthe combined organic phases were washed with brine
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was removed in vacuo
  6. customThe crude product was purified by flash chromatography (300 g silica gel; cyclohexane/EA, gradient from 100:0 to 50:50)

Sources & evidence

ORD record
ord-b0344d6bbcf34323b70aa3ba9e037cd7
Source dataset
uspto-grants-2011_12
Patent number
US08076324B2

Reaction notes

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