alpha-Chloro-m-nitrotoluene → HCID 4322234, compound

HRID 1405201Notes

Reaction equation

HRID 1405201 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH2:7]Cl)([O-:3])=[O:2].[C:12]1([S-:18])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[Na+]>C(O)C>[N+:1]([C:4]1[CH:11]=[CH:10][CH:9]=[C:6]([CH2:7][S:18][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:5]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 12078alpha-Chloro-m-nitrotolueneHCID 4110039Sodium benzenethiolate

Product 1

HCID 4322234HCID 4322234, compoundYield 102.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3-nitrobenzyl chloride (10.0 g) in ethanol (120 mL) was cooled to 0° C., treated with sodium thiophenolate (9.1 g, 90%) in 3 portions, while the temperature was slowly increased to room temperature the mixture was stirred for 18 hours. The reaction mixture was then concentrated in vacuo, treated with diethyl ether (350 mL), washed with water (2×150 mL) and brine (100 mL), dried with sodium sulfate and evaporated to dryness. The title compound (14.6 g) was thus obtained and used without further purification.

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. additiontreated with diethyl ether (350 mL)
  3. washwashed with water (2×150 mL) and brine (100 mL)
  4. dry with materialdried with sodium sulfate
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-94b544f29bda4ae79986eb7a4f8f2883
Source dataset
uspto-grants-2014_12
Patent number
US08916557B2

Reaction notes

Loading…