Aniline → HCID 136332823, compound

HRID 1643325Notes

Reaction equation

HRID 1643325 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:8]([O-])=O.[Na+].[CH3:12][C:13]1[CH:18]=[CH:17][C:16]([SH:19])=[CH:15][CH:14]=1>Cl.O.[OH-].[Na+]>[C:2]1([N:1]=[N:8][C:15]2[CH:14]=[C:13]([CH3:12])[CH:18]=[CH:17][C:16]=2[SH:19])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 6115AnilineHCID 78114-MethylbenzenethiolHCID 23668193Sodium Nitrite

Product 1

HCID 136332823HCID 136332823, compoundYield 61.4%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolvent2×HCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

5 g (53.7 mmoles) of aniline is dissolved in conc. HCl (13 ml)/water (90 ml) and diazotized with 3.89 g (56.4 mmoles) of sodium nitrite (dissolved in water (8 ml)), at 0-5° C. The resulting solution is slowly added to a solution of 7.52 g (53.7 mmoles) of 4-methylthiophenol in 2N NaOH (54 ml). After stirring overnight the mixture is neutralised with 2N HCl, the precipitate is filtered off, dried, and dissolved in toluene (800 ml). The solution is dried over anhydrous sodium sulfate, filtered through silica gel, and evaporated. Recrystallisation from methanol gives 7.53 g (57%) of dark brown crystals, m.p. 70-80° C.

Workup

  1. filtrationthe precipitate is filtered off
  2. customdried
  3. dissolutiondissolved in toluene (800 ml)
  4. dry with materialThe solution is dried over anhydrous sodium sulfate
  5. filtrationfiltered through silica gel
  6. customevaporated
  7. customRecrystallisation from methanol

Sources & evidence

ORD record
ord-37c2edc7a8df4906bf03017d3319f8e3
Source dataset
uspto-grants-2012_02
Patent number
US08119778B2

Reaction notes

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