Iodoethane → 2-Chloro-4-(ethylthio)benzenamine

HRID 2072591Notes

Reaction equation

HRID 2072591 reaction equation
[Cl:1][C:2]1[CH:8]=[C:7]([S:9][C:10]#N)[CH:6]=[CH:5][C:3]=1[NH2:4].O.O.O.O.O.O.O.O.O.[S-2].[Na+].[Na+].[CH2:24](I)C>C(O)C.O>[Cl:1][C:2]1[CH:8]=[C:7]([S:9][CH2:10][CH3:24])[CH:6]=[CH:5][C:3]=1[NH2:4]

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 73972Sodium sulfide nonahydrateHCID 591125((4-Amino-3-chlorophenyl)sulfanyl)formonitrile

Product 1

HCID 198585732-Chloro-4-(ethylthio)benzenamine

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
50 °C

Procedure

A solution of 2-chloro-4-thiocyanoaniline (40 g., 0.22 mole) in ethanol (250 ml.) is added to a stirred solution of sodium sulfide nonahydrate (58.5 g., 0.22 mole) in water (110 ml.) and the mixture is warmed (50° C.) for 45 minutes. Ethyl iodide (36.6 g., 0.22 mole) is added and stirring is continued for 2 hours at 50° C. and then at room temperature overnight. The reaction is poured into water (3 liters) and the product extracted with either. The combined extracts are washed with water and dried (CaSO4). Removal of the drying agent and solvent gives 2-chloro-4-ethylthioaniline, an oil.

Workup

  1. customat room temperature
  2. customovernight
  3. extractionthe product extracted with either
  4. washThe combined extracts are washed with water
  5. dry with materialdried (CaSO4)
  6. customRemoval of the drying agent and solvent

Sources & evidence

ORD record
ord-4efb5348893b43859c817e4dea8a8d95
Source dataset
uspto-grants-1990_04
Patent number
US04913728

Reaction notes

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