Thiophenol → 2-Nitro-5-phenylthioaniline

HRID 1679445Notes

Reaction equation

HRID 1679445 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6](Cl)[CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[CH:12]1[CH:17]=[CH:16][C:15]([S-:18])=[CH:14][CH:13]=1.[Na+].[H-].[Na+].C1(S)C=CC=CC=1>CN(C)C=O>[NH2:1][C:2]1[CH:7]=[C:6]([S:18][C:15]2[CH:16]=[CH:17][CH:12]=[CH:13][CH:14]=2)[CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10]

Participants

6

Reactant 4

HCID 7969ThiophenolHCID 24758Sodium hydrideHCID 742185-Chloro-2-nitroanilineHCID 4110039Sodium benzenethiolate

Product 1

HCID 1707372-Nitro-5-phenylthioaniline

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5 G. of 2-amino-4-chloro-1-nitrobenzene is added to a solution of sodium phenyl mercaptide, prepared under nitrogen from 2.53 g. 57% sodium hydride and 6.2 ml. thiophenol in 20 ml. dimethylformamide, with a 10 ml. dimethylformamide rinse. The mixture is stirred under nitrogen for 3 hours at 20°-30° C and then diluted with water. The crude product is washed with water and hexane, then recrystallized from methanol, yielding 2-amino-4-phenylthio-1-nitrobenzene.

Workup

  1. customprepared under nitrogen from 2.53 g
  2. washdimethylformamide rinse
  3. additiondiluted with water
  4. washThe crude product is washed with water and hexane
  5. customrecrystallized from methanol

Sources & evidence

ORD record
ord-aa60eba55f2d4cae90558e1981f9824f
Source dataset
uspto-grants-1978_03
Patent number
US04080461

Reaction notes

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