Sodium Hydroxide → 2-Chloro-4-nitrobenzene-1-thiol

HRID 856700Notes

Reaction equation

HRID 856700 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1Br.[S:12]([O-])([O-])(=O)=O.[Na+].[Na+].[S].[OH-].[Na+]>C(O)C>[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[SH:12]

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 24436Sodium SulfateHCID 346671-Bromo-2-chloro-4-nitrobenzeneHCID 5362487Sulfur

Product 1

HCID 3057302-Chloro-4-nitrobenzene-1-thiolYield 58.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

2-chloro-4-nitro-bromobenzene (20 g) was dissolved in ethanol (160 ml), and an aqueous solution of sodium sulfate nanohydrate (15.2 g) and sulfur (2.0 g) in ethanol (200 ml) was added dropwise to the solution for 20 minutes under heat reflux. An aqueous solution of sodium hydroxide (5.1 g, 20.3 ml) was added dropwise to the solution for 20 minutes, and then, the mixture was cooled to room temperature, and ice-water was added thereto. The precipitates were filtered, and the pH of the filtrate was adjusted to about pH 5 with 6N hydrochloric acid, and the precipitates were collected by filtration and washed with water to give 2-chloro-4-nitrobenzenethiol (9.4 g).

Workup

  1. temperatureunder heat
  2. temperaturereflux
  3. filtrationThe precipitates were filtered
  4. filtrationthe precipitates were collected by filtration
  5. washwashed with water

Sources & evidence

ORD record
ord-03ca1855bbdb4537a14c920ca16daba2
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

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