p-Toluenesulfonic acid → HCID 22125017, compound

HRID 1858194Notes

Reaction equation

HRID 1858194 reaction equation
[C:1]1([NH:7][C:8]2[C:13]([CH:14]=S)=[CH:12][N:11]=[C:10](C)[N:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:17][C:18]1[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[C:19]=1[NH2:20].C1(C)C=C[C:29]([S:32](O)(=O)=O)=CC=1.[BH4-].[Na+]>C1(C)C=CC=CC=1.CO.O>[Cl:17][C:18]1[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[C:19]=1[NH:20][CH2:14][C:13]1[C:8]([NH:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[N:9][C:10]([S:32][CH3:29])=[N:11][CH:12]=1

Participants

8

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 118462,6-DichloroanilineHCID 4311764Sodium borohydrideHCID 86756052HCID 86756052, compound

Product 1

HCID 22125017HCID 22125017, compoundYield 209.5%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A mixture of 700 mg (2.9 mmol) of 4-phenylamino-2-methylthiopyrimidine-5-carboxaldehyde, 490 mg (3.0 mmol) of 2,6-dichloroaniline and 100 mg (0.5 mmol) of 4-toluenesulfonic acid in 50 ml of toluene was heated at reflux with the azeotropic removal of water for 18 hours. The mixture was cooled and evaporated. 50 ml of methanol and 400 mg (11.7 mmol) of sodium borohydride were added and the mixture was heated at reflux for 20 minutes, cooled and then evaporated. The residue was stirred in a mixture of 50 ml of 2M aqueous sodium hydroxide and 50 ml of ethyl acetate for 30 minutes and then the phases were separated. The organic phase was dried over magnesium sulfate, filtered and evaporated. Flash chromatography of the residue on silica gel using diethyl ether/hexane (2:3) for the elution gave 410 mg (36%) of 5-(2,6-dichlorophenyl)aminomethyl-4-phenylamino-2-methylthiopyrimidine as a white solid.

Workup

  1. temperaturewas heated
  2. temperatureThe mixture was cooled
  3. customevaporated
  4. temperaturethe mixture was heated
  5. temperatureat reflux for 20 minutes
  6. temperaturecooled
  7. customevaporated
  8. customthe phases were separated
  9. dry with materialThe organic phase was dried over magnesium sulfate
  10. filtrationfiltered
  11. customevaporated
  12. washfor the elution

Sources & evidence

ORD record
ord-148efbd2860e4eaf993c5180e20c0914
Source dataset
uspto-grants-2000_11
Patent number
US06150373

Reaction notes

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