Diethyl Ether → Amino-3-[2-(4-cyanophenyl)ethylthio]benzene

HRID 325041Notes

Reaction equation

HRID 325041 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([SH:8])[CH:5]=[CH:6][CH:7]=1.[C:9]([C:11]1[CH:16]=[CH:15][C:14]([CH2:17][CH2:18]OS(C2C=CC(C)=CC=2)(=O)=O)=[CH:13][CH:12]=1)#[N:10].C([O-])([O-])=O.[K+].[K+].CCOCC>CCO.C(Cl)Cl>[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([S:8][CH2:18][CH2:17][C:14]2[CH:15]=[CH:16][C:11]([C:9]#[N:10])=[CH:12][CH:13]=2)[CH:3]=1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 11430Potassium CarbonateHCID 315773-AminothiophenolHCID 22033501HCID 22033501, compound

Product 1

HCID 22033546Amino-3-[2-(4-cyanophenyl)ethylthio]benzeneYield 49%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

3-Aminothiophenol (0.87 g; 7.0 mmol), 4-toluenesulfonic acid-2-(4-cyano-phenyl) ethyl ester (2.0 g; 6.6 mmol; from step (i) above) and K2CO3 (1 g) were stirred in a mixture of EtOH (10 mL) and CH2Cl2 for 4 hours. Addition of ether, washing with brine and 2M aqueous NaOH, drying (MgSO4), evaporation of the solvent and flash chromatography (SiO2; Et2O:hexane (1:1)) afforded 0.82 g (49%) of the sub-title compound.

Workup

  1. washwashing with brine and 2M aqueous NaOH
  2. customdrying
  3. custom(MgSO4), evaporation of the solvent and flash chromatography (SiO2; Et2O:hexane (1:1))

Sources & evidence

ORD record
ord-5fb81c08a4a84b14bfa1ca90758e419a
Source dataset
uspto-grants-2001_04
Patent number
US06221898B1

Reaction notes

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