Water → 5-(Benzylsulfanyl)-2-chloroaniline

HRID 1512998Notes

Reaction equation

HRID 1512998 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:6]([SH:9])=[CH:5][C:3]=1[NH2:4].[CH2:10](Br)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH2:10]([S:9][C:6]1[CH:7]=[CH:8][C:2]([Cl:1])=[C:3]([CH:5]=1)[NH2:4])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 6406993-amino-4-chlorobenzenethiol

Product 1

HCID 580219835-(Benzylsulfanyl)-2-chloroaniline

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-chloro-5-mercaptoaniline (0.64 g) and benzyl bromide (0.52 mL) in N,N-dimethylformamide (10 mL) was added potassium carbonate (0.61 g), and the mixture was stirred at room temperature for 1 hour. The reaction mixture was poured into water, and the resulting mixture was extracted with ethyl acetate. The extract was washed with water and brine, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: n-hexane−n-hexane/ethyl acetate=7/3) to give the title compound (0.37 g).

Workup

  1. extractionthe resulting mixture was extracted with ethyl acetate
  2. washThe extract was washed with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was purified by column chromatography on silica gel (eluent: n-hexane−n-hexane/ethyl acetate=7/3)

Sources & evidence

ORD record
ord-d30f638776364abe9f903df47e0117f1
Source dataset
uspto-grants-2012_07
Patent number
US08217069B2

Reaction notes

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