p-Toluenesulfonic acid → HCID 20531397, compound

HRID 2354522Notes

Reaction equation

HRID 2354522 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[SH:9].[Br:10][C:11]1[CH:18]=[CH:17][C:14]([CH:15]=O)=[CH:13][CH:12]=1.CC1C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Br:10][C:11]1[CH:18]=[CH:17][C:14]([C:15]2[S:9][C:3]3[CH:4]=[C:5]([CH3:8])[CH:6]=[CH:7][C:2]=3[N:1]=2)=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 707414-BromobenzaldehydeHCID 3232602-Amino-5-methylbenzene-1-thiol

Product 1

HCID 20531397HCID 20531397, compoundYield 76.94%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2-amino-5-methylthiophenol 10.02 g (72 mmole), 4-bromobenzaldehyde 16 g (87 mmole), and 2.8 g of PTSA (14 mmole) was stirred in 150 ml of Toluene, the reaction mixture was then heated to reflux for 16 hours, after cooling, the reaction mixture was extracted with water, and then the organic layer was evaporated to dry, the residue was then recrystallized with acetone to get 16.85 g of product (yield=76.94%).

Workup

  1. temperaturethe reaction mixture was then heated
  2. temperatureto reflux for 16 hours
  3. temperatureafter cooling
  4. extractionthe reaction mixture was extracted with water
  5. customthe organic layer was evaporated
  6. customto dry
  7. customthe residue was then recrystallized with acetone

Sources & evidence

ORD record
ord-1b895fe8f8f44eceb6d1e762ee07371a
Source dataset
uspto-grants-2010_07
Patent number
US07754348B2

Reaction notes

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