2,3-Dichloropropene → 4-Chloro-2-fluoro-5-(2-chloro-2-propenylthio)aniline

HRID 1681092Notes

Reaction equation

HRID 1681092 reaction equation
[NH2:1][C:2]1[C:3]([F:10])=[CH:4][C:5]([Cl:9])=[C:6]([SH:8])[CH:7]=1.[Cl:11][C:12]([CH2:14]Cl)=[CH2:13]>CN(C)C=O>[Cl:9][C:5]1[C:6]([S:8][CH2:14][C:12]([Cl:11])=[CH2:13])=[CH:7][C:2]([NH2:1])=[C:3]([F:10])[CH:4]=1

Participants

4

Reactant 2

HCID 65652,3-DichloropropeneHCID 11019406Benzenethiol, 5-amino-2-chloro-4-fluoro-

Product 1

HCID 198069724-Chloro-2-fluoro-5-(2-chloro-2-propenylthio)anilineYield 84%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 5-amino-2-chloro-4-fluorothiophenol (8.89 g) and anhydride potassium carbonate (3.5 g) was dissolved in N,N-dimethylformamide (100 ml), and 2,3-dichloropropene (6.65 g) was added thereto. The resultant mixture was stirred at 20° to 40° C. for 4 hours. After completion of the reaction, the reaction mixture was extracted with ether,washed with water, dried and concentrated. The residue was purified by silica gel chromatography (eluent: hexane/ethyl acetate=7/1) to give 4-chloro-2-fluoro-5-(2-chloro-2-propenylthio)aniline (10.5 g; yield, 84%).

Workup

  1. customAfter completion of the reaction
  2. extractionthe reaction mixture was extracted with ether,washed with water
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel chromatography (eluent: hexane/ethyl acetate=7/1)

Sources & evidence

ORD record
ord-b584542169194b5a987aea148c08a44a
Source dataset
uspto-grants-1992_12
Patent number
US05169431

Reaction notes

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