Potassium Carbonate → 4-Chloro-5-(5-isoquinolylsulfanyl)-2-nitroaniline

HRID 619729Notes

Reaction equation

HRID 619729 reaction equation
[CH:1]1[C:10]2[CH:9]=[CH:8][CH:7]=[C:6]([SH:11])[C:5]=2[CH:4]=[CH:3][N:2]=1.C(=O)([O-])[O-].[K+].[K+].[Cl:18][C:19]1[C:25](Cl)=[CH:24][C:22]([NH2:23])=[C:21]([N+:27]([O-:29])=[O:28])[CH:20]=1>CN(C=O)C>[Cl:18][C:19]1[C:25]([S:11][C:6]2[CH:7]=[CH:8][CH:9]=[C:10]3[C:5]=2[CH:4]=[CH:3][N:2]=[CH:1]3)=[CH:24][C:22]([NH2:23])=[C:21]([N+:27]([O-:29])=[O:28])[CH:20]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 811494,5-Dichloro-2-nitroanilineHCID 110519635-Isoquinolinethiol

Product 1

HCID 218469034-Chloro-5-(5-isoquinolylsulfanyl)-2-nitroanilineYield 98.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-Isoquinolinethiol 500 mg (3.1 mmol) was dissolved in DMF 15 ml, potassium carbonate 830 mg (6.0 mmol) and 4,5-dichloro-2-nitroaniline 620 mg (3.0 mmol) were added, and the mixture was stirred at room temperature for 1.5 hours. The reaction mixture was poured into ice water, and the resulting precipitates were collected and washed with water to give 4-chloro-5-(5-isoquinolylsulfanyl)-2-nitroaniline 980 mg (98.4%).

Workup

  1. customthe resulting precipitates
  2. customwere collected
  3. washwashed with water

Sources & evidence

ORD record
ord-2aa0d5973a264f50a9117edd28e1e3fd
Source dataset
uspto-grants-1999_09
Patent number
US05959107

Reaction notes

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